Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines
作者：
Liang, Dong;Tan, Li-Ping;Xiao, Wen-Jing* ;Chen, Jia-Rong*
期刊：
Chemical Communications ,2020年56(26):3777-3780 ISSN：1359-7345
通讯作者：
Xiao, Wen-Jing;Chen, Jia-Rong
作者机构：
[Tan, Li-Ping; Xiao, WJ; Chen, Jia-Rong; Xiao, Wen-Jing; Liang, Dong] Cent China Normal Univ, Coll Chem, Minist Educ, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构：
[Xiao, WJ; Chen, JR] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, Coll Chem, Minist Educ, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
摘要：
A [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with formaldimines is described for the synthesis of perfluoroalkylated tetrahydroquinazolines. Key to this process is the photocatalytic radical-mediated generation of aza-o-QMs from 2-vinylanilines and perfluoroalkyl radical precursors as well as the in situ release of formaldimines from 1,3,5-triazinanes.
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英文
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Asymmetric Deoxygenative Cyanation of Benzyl Alcohols Enabled by Synergistic Photoredox and Copper Catalysis
作者：
Chen, Hong-Wei;Lu, Fu-Dong;Cheng, Ying* ;Jia, Yue;Lu, Liang-Qiu* ;...
期刊：
中国化学 ,2020年38(12):1671-1675 ISSN：1001-604X
通讯作者：
Cheng, Ying;Lu, Liang-Qiu
作者机构：
[Lu, Fu-Dong; Lu, Liang-Qiu; Cheng, Ying; Jia, Yue; Xiao, Wen-Jing; Chen, Hong-Wei; Lu, LQ] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Minist Educ,Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China.
通讯机构：
[Cheng, Y; Lu, LQ] C;Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Minist Educ,Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
Deoxygenative cyanation;Synergistic catalysis;Photocatalysis;Enantioselectivity;Chiral nitrile
摘要：
Summary of main observation and conclusion. An enantioselective deoxygenative cyanation of benzyl alcohols was accomplished for the first time through the synergistic photoredox and copper catalysis. This reaction features the use of organic photosensitizer and low-cost 3d metal catalyst, simple and safe operations, and extremely mild conditions. A variety of chiral benzyl nitriles were produced in generally good yields and high level of enantiocontrols from readily available feedstocks (22 examples, up to 93% yield and 92% ee). © 2020 SIOC, CAS, Shanghai and Wiley-VCH GmbH
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英文
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Light opens a new window for N-heterocyclic carbene catalysis
作者：
Liu, Jing;Xing, Xiao-Ning;Huang, Jin-Hai;Lu, Liang-Qiu* ;Xiao, Wen-Jing*
期刊：
CHEMICAL SCIENCE ,2020年11(39):10605-10613 ISSN：2041-6520
通讯作者：
Lu, Liang-Qiu;Xiao, Wen-Jing
作者机构：
[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Liu, Jing; Xiao, Wen-Jing; Huang, Jin-Hai] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xing, Xiao-Ning] Anyang Acad Agr Sci, 833 Wenming Rd, Anyang, Henan, Peoples R China.
通讯机构：
[Lu, LQ; Xiao, WJ] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要：
N-Heterocyclic carbenes (NHCs) are efficient Lewis basic catalysts for the umpolung of various polarized unsaturated compounds usually including aldehydes, imines, acyl chlorides and activated esters. NHC catalysis involving electron pair transfer steps has been extensively studied; however, NHC catalysis through single-electron transfer (SET) processes, despite having the potential to achieve chemical transformations of inert chemical bonds and using green reagents, has long been a challenging task in organic synthesis. In parallel, visible-light-induced photocatalysis and photoexcitation have been established as powerful tools to facilitate sustainable organic synthesis, as they enable the generation of various reactive radical intermediates under extremely mild conditions. Recently, a number of elegant visible-light-induced, NHC-catalyzed transformations were developed for accessing valuable organic compounds. As a result, this minireview will highlight the recent advances in this field.
语种：
英文
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When Light Meets Nitrogen-Centered Radicals: From Reagents to Catalysts
作者：
Yu, Xiao-Ye;Zhao, Quan-Qing;Chen, Jun;Xiao, Wen-Jing;Chen, Jia-Rong*
期刊：
ACCOUNTS OF CHEMICAL RESEARCH ,2020年53(5):1066-1083 ISSN：0001-4842
通讯作者：
Chen, Jia-Rong
作者机构：
[Zhao, Quan-Qing; Xiao, Wen-Jing; Chen, Jun; Chen, Jia-Rong; Yu, Xiao-Ye] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, Wuhan 430079, Hubei, Peoples R China.
摘要：
ConspectusNitrogen-centered radicals (NCRs) are a versatile class of highly reactive species that have a longer history than the classical carbon-based radicals in synthetic chemistry. Depending on the N-hybridization and substitution patterns, NCRs can serve as electrophiles or nucleophiles to undergo various radical transformations. Despite their power, progress in nitrogen-radical chemistry is still slow compared with the popularity of carbon radicals, and their considerable synthetic potential has been largely underexplored, which is, as concluded by Zard, mainly hampered by "a dearth of convenient access to these species and a lack of awareness pertaining to their reactivity".Over the past decade, visible-light photoredox catalysis has been established as a powerful toolbox that synthetic chemists can use to generate a diverse range of radical intermediates from native organic functional groups via a single electron transfer process or energy transfer under mild reaction conditions. This catalytic strategy typically obviates the need for external stoichiometric activation reagents or toxic initiators and often enables traditionally inaccessible ionic chemical reactions. On the basis of our long-standing interest in nitrogen chemistry and catalysis, we have emphasized the use of visible-light photoredox catalysis as a tactic to discover and develop novel methods for generating NCRs in a controlled fashion and synthetic applications. In this Account, we describe our recent advances in the development of visible-light-driven photoredox-catalyzed generation of NCRs and their synthetic applications.Inspired by the natural biological proton-coupled electron transfer (PCET) process, we first developed a strategy of visible-light-driven photoredox-catalyzed oxidative deprotonation electron transfer to activate the N-H bonds of hydrazones, benzamides, and sulfonamides to give the corresponding NCRs under mild reaction conditions. With these reactive species, we then achieved a range of 5-exo and 6-endo radical cyclizations as well as cascade reactions in a highly regioselective manner, providing access to a variety of potentially useful nitrogen heterocycles. To further expand the repertoire of possible reactions of NCRs, we also revealed that iminyl radicals, derived from O-acyl cycloalkanone oxime esters, can undergo facile ring-opening C-C bond cleavage to give cyanoalkyl radicals. These newly formed radical species can further undergo a variety of C-C bond-forming reactions to allow the synthesis of diverse distally functionalized alkyl nitriles. Stimulated by these studies, we further developed a wide variety of visible-light-driven copper-catalyzed radical cross-coupling reactions of cyanoalkyl radicals. Because of their inherent highly reactive and transient properties, the strategy of heteroatom-centered radical catalysis is still largely underexplored in organic synthesis. Building on our understanding of the fundamental chemistry of NCRs, we also developed for the first time the concept of NCR covalent catalysis, which involves the use of in situ-photogenerated NCRs to activate allyl sulfones, vinylcyclopropanes, and N-tosyl vinylaziridines. This catalytic strategy has thus enabled efficient difunctionalization of various alkenes and late-stage modification of complex biologically active molecules.In this Account, we describe a panoramic picture of our recent contributions since 2014 to the development and application of the visible-light-driven photoredox systems in the field of NCR chemistry. These studies provide not only efficient methods for the synthesis of functionally rich molecules but also some insight into the exploration of new reactivity or reaction modes of NCRs. © 2020 American Chemical Society.
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当时明月在又照君归来——忆张景龄教授
作者：
孙煜林;肖文精
期刊：
武汉文史资料 ,2020年(7):21-23 ISSN：1004-1737
作者机构：
华中师范大学化学学院;[肖文精; 孙煜林] 华中师范大学
摘要：
我国著名的有机磷化学家、教育家,华中师范大学教授、博士生导师张景龄先生离开我们已经近30年了.他毕生致力于人才培养和科学研究事业,创建了华中师范大学农药化学研究所和农药学学科,培养了几代科技创新人才,为我国有机磷化学和农药化学的教育和研究作出了杰出贡献.
语种：
中文
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Visible light-promoted ring-opening functionalization of three-membered carbo- And heterocycles
作者：
Xuan, Jun* ;He, Xiang-Kui;Xiao, Wen-Jing*
期刊：
CHEMICAL SOCIETY REVIEWS ,2020年49(9):2546-2556 ISSN：0306-0012
通讯作者：
Xuan, Jun;Xiao, Wen-Jing
作者机构：
[Xuan, Jun; He, Xiang-Kui] Anhui Univ, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Coll Chem & Chem Engn, Hefei 230601, Anhui, Peoples R China.;[Xuan, Jun] Anhui Univ, Key Lab Struct & Funct Regulat Hybrid Mat, Minist Educ, Hefei 230601, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Xuan, Jun] A;[Xiao, Wen-Jing] C;Anhui Univ, Anhui Prov Key Lab Chem Inorgan Organ Hybrid Func, Coll Chem & Chem Engn, Hefei 230601, Anhui, Peoples R China.;Anhui Univ, Key Lab Struct & Funct Regulat Hybrid Mat, Minist Educ, Hefei 230601, Peoples R China.;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要：
Due to their inherent ring strain, three-membered carbocyclic- and heterocyclic ring structures are versatile synthetic building blocks. Traditional ring-opening methods of these molecules require the use of thermolysis, acid catalysts or transition-metals via ionic reaction pathways. Recently, visible light-induced photoredox catalysis has emerged as a powerful platform for initiating new chemical transformations. In this tutorial review, the synthetic and mechanistic aspects of visible light-promoted ring-opening functionalization of three-membered carbo- and heterocycles are highlighted. By using these strategies, a variety of ring-opening functionalization products, including biologically important carbo- and heterocycles, can be efficiently accessed in a high chemo- and regioselective manner. © 2020 The Royal Society of Chemistry.
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英文
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Recent Progress in Applications of Vinylaziridines in Organic Synthesis [乙烯基氮杂环丙烷在有机合成中的研究进展]
作者：
Wu Yali;Zhou Xuesong;Xiao Wenjing;Chen Jiarong*
期刊：
有机化学 ,2020年40(11):3760-3776 ISSN：0253-2786
通讯作者：
Chen Jiarong
作者机构：
[Zhou Xuesong; Chen Jiarong; Wu Yali; Xiao Wenjing] Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China.
通讯机构：
[Chen Jiarong] C;Cent China Normal Univ, Coll Chem, Wuhan 430079, Peoples R China.
关键词：
乙烯基氮杂环丙烷;氮杂环丙烷;开环反应;环化反应;氮杂环合成
摘要：
乙烯基氮杂环丙烷是有机合成化学中一类重要的合成砌块,由于同时含有烯烃和具有较强张力的氮杂环丙烷官能团,乙烯基氮杂环丙烷有着丰富的反应活性,能够发生多种化学反应.这些反应被广泛用于各种含氮分子,尤其是含氮杂环的合成,如氮杂环丁烷、吡咯烷、哌啶和氮杂环庚烷等杂环化合物.另外,各种取代的乙烯基氮杂环丙烷的简单、高效合成方法的发展,进一步推动了这类试剂在有机合成、医药、农药和化工等领域的应用.近年来,这类试剂仍然一直吸引着众多研究者的兴趣,在有机合成化学领域取得了快速发展.对近五年来乙烯基氮杂环丙烷参与的亲核性开环反应和环化反应进行了综述,并对该领域的发展方向进行了展望.
语种：
中文
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C,N-环状偶氮次甲基亚胺参与的反应研究进展
作者：
Hua Tingbi;Yang Qingqing* ;Xiao Wengjing*
期刊：
有机化学 ,2020年40(11):3559-3595 ISSN：0253-2786
通讯作者：
Yang Qingqing;Xiao Wengjing
作者机构：
[Hua Tingbi; Yang Qingqing] China Thin Gorges Univ, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Hubei, Peoples R China.;[Hua Tingbi; Yang Qingqing] China Thin Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, Yichang 443002, Hubei, Peoples R China.;[Xiao Wengjing] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Yang Qingqing; Xiao Wengjing] C;China Thin Gorges Univ, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Hubei, Peoples R China.;China Thin Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, Yichang 443002, Hubei, Peoples R China.;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词：
3-偶极子;偶氮次甲基亚胺;N-环状偶氮次甲基亚胺;环加成反应;异喹啉衍生物
摘要：
在环状偶氮次甲基亚胺类1,3-偶极子中,C,N-环状偶氮次甲基亚胺是使用最广泛的反应试剂,用于结构多样化的四氢异喹啉衍生物的构建.简单综述了C,N-环状偶氮次甲基亚胺参与的反应研究进展,重点介绍[3+2]、[3+3]、[3+4]、[5+1]、[3+1]环加成以及其他反应,并讨论了反应的特点、反应过程及合成应用,最后展望了它的发展前景.
语种：
中文
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Visible-light-induced triple catalysis for a ring-opening cyanation of cyclopropyl ketones
作者：
Liu, Jing;Liu, Xiao-Peng;Wu, Hong;Wei, Yi;Lu, Fu-Dong;...
期刊：
Chemical Communications ,2020年56(77):11508-11511 ISSN：1359-7345
通讯作者：
Cheng, Ying;Xiao, Wen-Jing
作者机构：
[Cheng, Ying; Xiao, WJ; Lu, Fu-Dong; Liu, Jing; Guo, Kai-Rui; Xiao, Wen-Jing; Liu, Xiao-Peng; Wu, Hong; Wei, Yi] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构：
[Cheng, Y; Xiao, WJ] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
摘要：
An unprecedented triple catalytic, general ring-opening cyanation reaction of cyclopropyl ketones for the construction of γ-cyanoketones is described. The key is to merge photoredox catalysis with Lewis acid catalysis and copper catalysis to enable the selective cleavage of the carbon-carbon bonds and the selective coupling of the generated radical and cyanide anion. © The Royal Society of Chemistry 2020.
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英文
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Recent Advances of 1,3,5-Triazinanes in Aminomethylation and Cycloaddition Reactions
作者：
Liang, Dong;Xiao, Wen-Jing;Chen, Jia-Rong*
期刊：
SYNTHESIS-STUTTGART ,2020年52(17):2469-2482 ISSN：0039-7881
通讯作者：
Chen, Jia-Rong
作者机构：
[Xiao, Wen-Jing; Chen, Jia-Rong; Liang, Dong] Cent China Normal Univ, Minist Educ, Coll Chem, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Chen, Jia-Rong] C;Cent China Normal Univ, Minist Educ, Coll Chem, CCNU uOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
hexahydro;triazines;triazinanes;formaldimines;aminomethylations;cycloadditions;nitrogen;containing compounds
摘要：
1,3,5-Trisubstituted 1,3,5-triazinanes (hexahydro-1,3,5-triazines), as stable and readily available surrogates for formaldimines, have found extensive applications for the construction of various nitrogen-containing compounds. The formaldimines, formed in situ from this reagent class, can participate in various aminomethylation and cycloaddition reactions. This short review presents recent advances in this field with emphasis on the conceptual ideas behind the developed methodologies and the reaction mechanisms.
1 Introduction
2 Aminomethylations with 1,3,5-Triazinanes
3 Cycloadditions with 1,3,5-Triazinanes
3.1 Use of 1,3,5-Triazinanes as Two-Atom Synthons
3.2 Use of 1,3,5-Triazinanes as Three-Atom Synthons
3.3 Use of 1,3,5-Triazinanes as Four-Atom Synthons
3.4 Use of 1,3,5-Triazinanes as Six-Atom Synthons
4 Conclusions
语种：
英文
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Radical carbonylative synthesis of heterocycles by visible light photoredox catalysis
作者：
Hu, Xiao-Qiang* ;Liu, Zi-Kui;Xiao, Wen-Jing*
期刊：
Catalysts ,2020年10(9):1-26 ISSN：2073-4344
通讯作者：
Hu, Xiao-Qiang;Xiao, Wen-Jing
作者机构：
[Liu, Zi-Kui; Hu, Xiao-Qiang] South Cent Univ Nationalities, Sch Chem & Mat Sci, Key Lab Catalysis & Energy Mat Chem, Minist Educ, Wuhan 430074, Peoples R China.;[Liu, Zi-Kui; Hu, Xiao-Qiang] South Cent Univ Nationalities, Sch Chem & Mat Sci, Hubei Key Lab Catalysis & Mat Sci, Wuhan 430074, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ CCNU, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
通讯机构：
[Hu, Xiao-Qiang] S;[Xiao, Wen-Jing] C;South Cent Univ Nationalities, Sch Chem & Mat Sci, Key Lab Catalysis & Energy Mat Chem, Minist Educ, Wuhan 430074, Peoples R China.;South Cent Univ Nationalities, Sch Chem & Mat Sci, Hubei Key Lab Catalysis & Mat Sci, Wuhan 430074, Peoples R China.;Cent China Normal Univ CCNU, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
关键词：
Acyl radical;Heterocycles;Radical carbonylation;Visible light photocatalysis
摘要：
Visible light photocatalytic radical carbonylation has been established as a robust tool for the efficient synthesis of carbonyl-containing compounds. Acyl radicals serve as the key intermediates in these useful transformations and can be generated from the addition of alkyl or aryl radicals to carbon monoxide (CO) or various acyl radical precursors such as aldehydes, carboxylic acids, anhydrides, acyl chlorides or α-keto acids. In this review, we aim to summarize the impact of visible light-induced acyl radical carbonylation reactions on the synthesis of oxygen and nitrogen heterocycles. The discussion is mainly categorized based on different types of acyl radical precursors. © 2020 by the authors. Licensee MDPI, Basel, Switzerland.
语种：
英文
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Tandem Phospha‐Michael Addition/N‐Acylation/ Intramolecular Wittig Reaction of aza‐o‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles
作者：
Hua, Ting-Bi;Chao, Fei;Wang, Long;Yan, Chen-Yang;Xiao, Cong;...
期刊：
ADVANCED SYNTHESIS & CATALYSIS ,2020年362(13):2615-2619 ISSN：1615-4150
通讯作者：
Yang, Qing-Qing;Xiao, Wen-Jing
作者机构：
[Hua, Ting-Bi; Wang, Long; Yang, Qing-Qing; Yan, Chen-Yang; Chao, Fei] China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.;[Hua, Ting-Bi; Yang, Qing-Qing] China Three Gorges Univ, Hubei Key Lab Nat Prod Res & Dev, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.;[Xiao, Cong] Wuhan Glycolipid Co Ltd, 666 East Lake High Tech Dev Zone, Wuhan 430075, Hubei, Peoples R China.;[Xiao, Wen-Jing] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
通讯机构：
[Yang, Qing-Qing; Xiao, Wen-Jing] C;China Three Gorges Univ, Coll Mat & Chem Engn, Key Lab Inorgan Nonmetall Crystalline & Energy Co, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.;China Three Gorges Univ, Hubei Key Lab Nat Prod Res & Dev, 8 Daxue Rd, Yichang 443002, Hubei, Peoples R China.;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
aza-o-Quinone Methides;Ιndoles;Intramolecular Wittig Reaction;Tandem Reaction;Phospha-Michael Addition
摘要：
A tandem phospha-Michael addition/N-acylation/intramolecular Wittig reaction of in situ formed aza-o-QMs is disclosed. This approach features high functional group tolerance and provides a convenient and practical access to biologically significant indole derivatives (37 examples, up to 91% yield) under mild reaction conditions. (Figure presented.). © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
语种：
英文
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Synergetic iridium and amine catalysis enables asymmetric [4+2] cycloadditions of vinyl aminoalcohols with carbonyls
作者：
Zhang, Mao-Mao;Wang, Ya-Ni;Wang, Bao-Cheng;Chen, Xiao-Wang;Lu, Liang-Qiu* ;...
期刊：
Nature Communications ,2019年10(1):1-9 ISSN：2041-1723
通讯作者：
Lu, Liang-Qiu;Xiao, Wen-Jing
作者机构：
[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Wang, Ya-Ni; Wang, Bao-Cheng; Xiao, Wen-Jing; Chen, Xiao-Wang; Zhang, Mao-Mao] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, CCNU uOttawa Joint Res Ctr, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Wang, Ya-Ni; Wang, Bao-Cheng; Xiao, Wen-Jing; Chen, Xiao-Wang; Zhang, Mao-Mao] Cent China Normal Univ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Lu, Liang-Qiu] Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Coll Chem & Chem Engn, Lanzhou 730000, Gansu, Peoples R China.
通讯机构：
[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, CCNU uOttawa Joint Res Ctr, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Cent China Normal Univ, Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.
摘要：
Catalytic asymmetric cycloadditions via transition-metal-containing dipolar intermediates are a powerful tool for synthesizing chiral heterocycles. However, within the field of palladium catalysis, compared with the well-developed normal electron-demand cycloadditions with electrophilic dipolarophiles, a general strategy for inverse electron-demand ones with nucleophilic dipolarophiles remains elusive, due to the inherent linear selectivity in the key palladium-catalyzed intermolecular allylations. Herein, based on the switched regioselectivity of iridium-catalyzed allylations, we achieved two asymmetric [4+2] cycloadditions of vinyl aminoalcohols with aldehydes and β,γ-unsaturated ketones through synergetic iridium and amine catalysis. The activation of vinyl aminoalcohols by iridium catalysts and carbonyls by amine catalysts provide a foundation for the subsequent asymmetric [4+2] cycloadditions of the resulting iridium-containing 1,4-dipoles and (di)enamine dipolarophiles. The former provides a straightforward route to a diverse set of enantio-enriched hydroquinolines bearing chiral quaternary stereocenters, and the later represent an enantio- and diastereodivergent synthesis of chiral hydroquinolines. © 2019, The Author(s).
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英文
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Photogenerated Neutral Nitrogen Radical Catalyzed Bifunctionalization of Alkenes
作者：
Zhao, Quan-Qing;Chen, Jun;Zhou, Xue-Song;Yu, Xiao-Ye;Chen, Jia-Rong* ;...
期刊：
CHEMISTRY-A EUROPEAN JOURNAL ,2019年25(34):8024-8029 ISSN：0947-6539
通讯作者：
Chen, Jia-Rong;Xiao, Wen-Jing
作者机构：
[Zhao, Quan-Qing; Chen, Jia-Rong; Xiao, WJ; Xiao, Wen-Jing; Chen, Jun; Zhou, Xue-Song; Yu, Xiao-Ye] Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticides & Chem Biol,Minist Educ,Coll C, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China.
通讯机构：
[Chen, JR; Xiao, WJ] C;[Xiao, Wen-Jing] S;Cent China Normal Univ, CCNU uOttawa Joint Res Ctr, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticides & Chem Biol,Minist Educ,Coll C, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China.
关键词：
alkene bifunctionalization;nitrogen radicals;photocatalysis;sulfones;visible light
摘要：
Alkene bifunctionalizations are powerful tools for the rapid construction of structurally complex and valuable scaffolds, and such reactions typically involve the use of transition-metal catalysts or organocatalysts. Here, we report for the first time a photogenerated neutral nitrogen radical catalyzed intermolecular alkene bifunctionalization by using allyl sulfones as the source of both the carbon and the sulfone functionalities under mild conditions. The key to the success of this protocol involves the visible-light-mediated photocatalytic in situ generation of a nitrogen-centered radical from the N-(2-acetylphenyl) benzenesulfonamide catalyst, and its activation of the allyl sulfones to generate reactive species. The preliminary control experiments supported the postulated mechanism. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
语种：
英文
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Photoinduced Copper-Catalyzed Radical Aminocarbonylation of Cycloketone Oxime Esters
作者：
Lu, Bin;Cheng, Ying;Chen, Li-Yan;Chen, Jia-Rong* ;Xiao, Wen-Jing
期刊：
ACS CATALYSIS ,2019年9(9):8159-8164 ISSN：2155-5435
通讯作者：
Chen, Jia-Rong
作者机构：
[Cheng, Ying; Lu, Bin; Xiao, Wen-Jing; Chen, Jia-Rong; Chen, Li-Yan] Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensing Technol, Key Lab Pesticides & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China.
通讯机构：
[Chen, Jia-Rong] C;Cent China Normal Univ, Int Joint Res Ctr Intelligent Biosensing Technol, Key Lab Pesticides & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词：
photochemistry;copper catalysis;radical carbonylation;aminocarbonylation;oxime esters;amides;nitriles
摘要：
A visible light-induced and exogenous photosensitizer-free, copper-catalyzed radical aminocarbonylation of cycloketone oxime esters with CO gas and amines is developed. The mild catalytic system involving CuCl and N,N,N-tridentate ligand shows good reactivity and chemoselectivity, and tolerates a wide range of cycloketone oxime esters and alkyl/aryl amines, giving the corresponding cyanoalkylated amides in moderate to good yields. Preliminary mechanistic studies suggest that the reaction involves a CuI/CuII/CuIII-based catalytic cycle and radical intermediate. © 2019 American Chemical Society.
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英文
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The Recent Developments of Photocatalytic Oxidation
作者：
Wei Ding;Liang-Qiu Lu;Wen-Jing Xiao
期刊：
Green Oxidation in Organic Synthesis ,2019年:383-408
作者机构：
[Wei Ding; Liang-Qiu Lu; Wen-Jing Xiao] College of Chemistry, Central China Normal University, Wuhan, China
关键词：
amine motif;imine;organic synthesis;oxidative reactions;photocatalytic oxidation;visible-light-mediated aerobic oxidation
摘要：
The development of green and sustainable methods for “effective” synthesis of fine chemicals is an important goal for synthetic organic chemists. Oxidative reactions are an important process in Nature and constitute one of the most fundamental chemical transformations in organic synthesis. This chapter highlights the recent advances of visible-light-mediated aerobic oxidation and oxygenation reactions. The amine motif is a kind of good electron donor due to the nitrogen atom possessing lone pair electron, and they are the most common reductive quenchers for the photoredox catalysis, particularly tertiary amines. Visible-light-induced photocatalytic oxidation reactions of amines using oxygen as an oxidant have attracted significant interest from organic chemists. The photocatalytically generated imine intermediates have been applied into a series of nucleophilic addition and cycloaddition reactions. Transition metal-catalyzed C–H oxidative functionalization has proven to be a powerful tool for the construction of complex organic molecules.
语种：
英文
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Exploration of a Chiral Cobalt Catalyst for Visible-Light-Induced Enantioselective Radical Conjugate Addition.
作者：
Zhang, Kai;Lu, Liang-Qiu* ;Jia, Yue;Wang, Ying;Lu, Fu-Dong;...
期刊：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION ,2019年58(38):13375-13379 ISSN：1433-7851
通讯作者：
Lu, Liang-Qiu;Xiao, Wen-Jing
作者机构：
[Lu, Fu-Dong; Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Jia, Yue; Xiao, Wen-Jing; Wang, Ying; Pan, Fangfang; Zhang, Kai] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China.
通讯机构：
[Lu, LQ; Xiao, WJ; Xiao, Wen-Jing] C;Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticide & Chem Biol,Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Collaborat Innovat Ctr Chem Sci & Engn, Tianjin 300072, Peoples R China.
关键词：
asymmetric catalysis;cobalt;Giese reaction;radicals;visible light
摘要：
Chiral catalysts tolerating photochemical reactions are in great demand for the vast development of visible-light-induced asymmetric synthesis. Now, chiral octahedral complexes based on earth-abundant metal and chiral N4 ligands are reported. One well-defined chiral CoII-complex is shown to be an efficient catalyst in the visible-light-induced conjugated addition of enones by alkyl and acyl radicals, providing synthetically valued chiral ketones and 1,4-dicarbonyls in 47–'99 % yields with up to 97:3 e.r. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
语种：
英文
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New Roles for Photoexcited Eosin Y in Photochemical Reactions
作者：
Dong-Mei Yan;Prof. Dr. Jia-Rong Chen;Prof. Dr. Wen-Jing Xiao
期刊：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION ,2019年58(2):378-380 ISSN：1433-7851
通讯作者：
Chen, Jia-Rong(chenjiarong@mail.ccnu.edu.cn)
作者机构：
[Dong-Mei Yan; Chen, Jia-Rong; Xiao, Wen-Jing] CCNU-uOttawa Joint Research Center, Key Laboratory of Pesticides & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan;Hubei;430079, China;[Dong-Mei Yan; Chen, Jia-Rong; Xiao, Wen-Jing] Hubei;[Dong-Mei Yan; Chen, Jia-Rong; Xiao, Wen-Jing] 430079, China
通讯机构：
[Prof. Dr. Jia-Rong Chen; Prof. Dr. Wen-Jing Xiao] C;CCNU-uOttawa Joint Research Center, Key Laboratory of Pesticides & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079 China
关键词：
C-H functionalization;eosin Y;hydrogen atom transfer;photoacids;photoredox catalysis
摘要：
Neutral eosin Y-derived photoexcited states have been found to serve as photoacids and direct hydrogen atom transfer (HAT) catalysts in the activation of glycals and C−H bonds, respectively. These studies pave the way for further use of eosin Y in photochemical synthesis. © 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
语种：
英文
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炔丙基自由基在有机合成化学中的应用
作者：
Lu Fu-Dong;Jiang Xuan;Lu Liang-Qiu* ;Xiao Wen-Jing*
期刊：
化学学报 ,2019年77(9):803-813 ISSN：0567-7351
通讯作者：
Lu Liang-Qiu;Xiao Wen-Jing
作者机构：
[Lu Liang-Qiu; Xiao, WJ; Lu Fu-Dong; Jiang Xuan; Xiao Wen-Jing] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 930079, Hubei, Peoples R China.;[Lu Liang-Qiu; Xiao, WJ; Lu Fu-Dong; Jiang Xuan; Xiao Wen-Jing] Cent China Normal Univ, Coll Chem, Wuhan 930079, Hubei, Peoples R China.;[Xiao Wen-Jing] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.
通讯机构：
[Lu, LQ; Xiao, WJ; Xiao Wen-Jing] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 930079, Hubei, Peoples R China.;Cent China Normal Univ, Coll Chem, Wuhan 930079, Hubei, Peoples R China.;Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.
关键词：
炔丙基自由基;炔丙位官能化;炔烃;联烯;过渡金属催化
摘要：
炔烃的合成与转化一直是有机合成化学的一个重要研究内容.其中,炔丙位官能化是实现炔烃合成与转化的一个重要途径.相对于经历阳离子中间体途径的炔丙位官能化反应,自由基途径的炔丙位官能化反应在最近十年才得以发展,且与前者也已形成互补之势.该类炔丙基自由基既能够通过炔丙位的碳杂键断裂生成,又可通过自由基对1,3-烯炔的加成生成.同时,由于炔丙基自由基存在自由基与炔烃的共轭结构,使得该自由基既能够直接对金属物种加成参与炔丙位的官能化反应,又能够异构成联烯自由基后对金属物种加成,继而参与联烯化合物的合成.此外,炔丙基自由基还可以被进一步氧化成炔丙基阳离子后参与后续的有机转化.本综述根据炔丙基自由基所参与的反应类型,对近年来炔丙位自由基参与的有机反应进行了简要总结.
语种：
中文
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A photoinduced Wolff rearrangement/Pd-catalyzed [3+2] cycloaddition sequence: an unexpected route to tetrahydrofurans.
作者：
Liu, Jie;Li, Miao-Miao;Qu, Bao-Le;Lu, Liang-Qiu* ;Xiao, Wen-Jing
期刊：
Chemical Communications ,2019年55(14):2031-2034 ISSN：1359-7345
通讯作者：
Lu, Liang-Qiu
作者机构：
[Liu, Jie; Lu, Liang-Qiu; Qu, Bao-Le; Xiao, Wen-Jing; Li, Miao-Miao] Cent China Normal Univ, Coll Chem, Minist Educ, CCNU UOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Lu, Liang-Qiu] Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.;[Xiao, Wen-Jing] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China.
通讯机构：
[Lu, Liang-Qiu] C;Cent China Normal Univ, Coll Chem, Minist Educ, CCNU UOttawa Joint Res Ctr,Key Lab Pesticide & Ch, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.
摘要：
A novel sequential reaction that combines a visible light-induced Wolff rearrangement of alpha-diazoketones and a Pd-catalyzed [3+2] cycloaddition of vinyl cyclopropanes with the resulting ketenes is described in this work. Selective O-allylic alkylation was observed over C-allylic alkylation, which unexpectedly led to a series of highly functionalized tetrahydrofurans with high efficiency (20 examples, 58-99% yields).
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英文
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