摘要:
A formal [3 + 2]-cycloaddition reaction of 2H-azirines with nitrosoarenes has been achieved under irradiation by visible light with the assistance of organic dye photoredox catalyst. This method utilizes nitrosoarenes as efficient radical acceptors and provides a green and powerful method for a series of biologically important 1,2,4-oxadiazole derivatives in moderate to good yields.
关键词:
metal carbonyls;carbonylation;carbonylative ring expansion;hydrofunctionalization;cycloaddition
摘要:
Still going strong in his seventies, Professor Howard Alper continues to make an impact on chemistry internationally. This Account highlights some of his key scientific achievements in catalysis. What began as a fundamental interest in the chemistry of metal carbonyls and their activity modes, evolved into a versatile program addressing some of the most significant and challenging issues in catalysis. Using well-defined metal carbonyl complexes, he and his lab were able to make fundamental insights into diverse transformations involving the catalytic properties of metal carbonyls, including carbonylative ring expansions. His creative and truly interdisciplinary research in catalysis has also resulted in notable contributions to carbonylation, hydrofunctionalization, and cycloaddition chemistry.
摘要:
The first cobalt-catalyzed deaminative alkoxycarbonylation reaction was described for the conversion of readily available primary alkyl amines to synthetically versatile esters with moderate to high yields. This transformation shows good functional group compatibility and can serve as a powerful tool for the modification of alkyl amine-containing complex natural products and drug molecules.
通讯作者:
Prof. Dr. Jia-Rong Chen<&wdkj&>Prof. Dr. Wen-Jing Xiao
作者机构:
[Dong-Mei Yan; Prof. Dr. Jia-Rong Chen; Prof. Dr. Wen-Jing Xiao] 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
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
摘要:
Neutrale angeregte Zustände von Eosin Y haben sich als nützliche Photosäuren sowie als Katalysatoren für den direkten Wasserstoffatomtransfer (“hydrogen atom transfer”, HAT) in der Aktivierung von Glykalen bzw. C‐H‐Bindungen erwiesen. Diese Untersuchungen ebenen den Weg für die weitere Verwendung von Eosin Y in der photochemischen Synthese. Neue Facetten von Eosin Y: Neutrale angeregte Zustände von Eosin Y haben sich als nützliche Photosäuren sowie als Katalysatoren für den direkten Wasserstoffatomtransfer („hydrogen atom transfer”, HAT) in der Aktivierung von Glykalen bzw. C‐H‐Bindungen erwiesen. Diese Untersuchungen ebnen den Weg für die weitere Verwendung von Eosin Y in photochemischen Synthesen.
作者机构:
[Lu, Liang-Qiu; Li, Tian-Ren; Wang, Ya-Ni; Xiao, Wen-Jing] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, CCNU UOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China.;[Lu, Liang-Qiu] Chinese Acad Sci, LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.
通讯机构:
[Lu, Liang-Qiu] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, CCNU UOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
关键词:
Benzoxazinone;Heterocycle synthesis;Dipolar cyclization;Transition metal catalysis
摘要:
Vinyl and ethynyl benzoxazinones have recently received increasing attention from organic chemists because they are powerful tools for the construction of structurally diverse aza-heterocycles. A number of catalytic cyclization reactions have been developed that used these two reagents and required the presence of a transition-metal catalyst (i.e., palladium, iron, and copper). This review highlights the design and synthesis of these versatile reagents, and their applications as precursors for transition metal-containing 1,4-dipoles in dipolar cyclizations and related cascade reactions. The general mechanisms and asymmetric inductions are briefly discussed as well. (C) 2018 Elsevier Ltd. All rights reserved.
作者机构:
[Lu, LQ; Xiao, WJ; Lu, Liang-Qiu; Xiao, Wen-Jing; Zhou, Quan-Quan; Ding, Wei; Wei, Yi; Liu, Dan] Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China.
通讯机构:
[Lu, LQ; Xiao, WJ] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China.
摘要:
A catalyst-controlled acylation reaction of β-ketoesters was developed for the first time by combining visible-light photoactivation with Lewis acid or base catalysis. By employing a NiCl2·glyme complex with a bis(oxazoline) ligand as the Lewis acid catalyst, C-acylation products are exclusively achieved, while utilizing pyridine or DABCO as the Lewis base catalyst affords O-acylation products with complete regioselectivity. A range of β-ketoesters with satisfactory structural diversity were suitable for this transformation, demonstrating the functional group compatibility of the method, which was attributed to the mild reaction conditions. This success is heavily built upon the visible-light-induced Wolff rearrangement and the unique catalytic activation modes, and thus, this work significantly expands the applications of ketene chemistry.
作者:
Ye, Hui;Xiao, Cong;Zhou, Quan-Quan;Wang, Peng George*;Xiao, Wen-Jing*
期刊:
JOURNAL OF ORGANIC CHEMISTRY,2018年83(21):13325-13334 ISSN:0022-3263
通讯作者:
Xiao, Wen-Jing;Wang, Peng George
作者机构:
[Ye, Hui; Xiao, Wen-Jing; Zhou, Quan-Quan] Cent China Normal Univ, Key Lab Pesticides & Chem Biol, CCNU uOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Ye, Hui; Xiao, Wen-Jing] Huanggang Normal Univ, Hubei Key Lab Proc & Applicat Catalyt Mat, Huanggang 438000, Peoples R China.;[Xiao, Cong; Wang, Peng George] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA.
通讯机构:
[Xiao, Wen-Jing] C;[Xiao, Wen-Jing] H;[Wang, Peng George] G;Cent China Normal Univ, Key Lab Pesticides & Chem Biol, CCNU uOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;Huanggang Normal Univ, Hubei Key Lab Proc & Applicat Catalyt Mat, Huanggang 438000, Peoples R China.
摘要:
Multifarious sugar lactols were efficiently transformed into the corresponding phenolic glycosides by treating with aryl bromides in acetonitrile with Ir[dF(CF3)ppy]2(dtbbpy)(PF6) as a photocatalyst under visible light irradiation. Both pyranoses and furanoses or even disaccharide could all suffer this glycosylation protocol under mild reaction conditions. A variety of phenyl glycosides can be produced in moderate to good yields (up to 93% yield), and a gram scale process of this protocol was also well-established.
作者机构:
[Lu, Fu-Dong; Lu, Liang-Qiu; Xiao, Wen-Jing; Zhou, Quan-Quan; Liu, Dan] Cent China Normal Univ, CCNU UOttawa Joint Res Ctr, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol,Minist Educ,Coll 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, Wen-Jing] C;[Xiao, Wen-Jing] L;Cent China Normal Univ, CCNU UOttawa Joint Res Ctr, Hubei Int Sci & Technol Cooperat Base Pesticide &, Key Lab Pesticide & Chem Biol,Minist Educ,Coll 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:
1,4-Benzodioxane widely exists as the core structure in many therapeutic agents and bioactive natural compounds. Hence, to access this kind of molecule, an enantioselective desymmetric C–O cross coupling reaction has been developed through dual visible light photoredox and nickel catalysis. Notably, the use of an axially chiral 2,2′-bipyridine ligand is the key to success. A series of chiral 1,4-benzodioxanes were afforded in high yields and moderate to good enantioselectivity under mild reaction conditions.
期刊:
Chemical Communications,2018年54(71):9925-9928 ISSN:1359-7345
通讯作者:
Chen, Jia-Rong;Xiao, Wen-Jing
作者机构:
[Li, Chan-Yun; Chen, Jia-Rong; Xiao, WJ; He, Bin-Qing; Xiao, Wen-Jing; Yu, Xiao-Ye; Wang, Peng-Zi] Cent China Normal Univ, Coll Chem, 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:
[Chen, JR; Xiao, WJ] C;[Xiao, Wen-Jing] S;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, 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.
摘要:
On the basis of the strategy of iminyl radical-mediated C-C bond cleavage, a visible light photocatalytic radical addition/cyclization cascade is described, providing an efficient and regioselective access to cyanoalkylated 1,2,3,4-tetrahydrophenanthrenes.
期刊:
Chemical Communications,2018年54(86):12262-12265 ISSN:1359-7345
通讯作者:
Chen, Jia-Rong
作者机构:
[He, Bin-Qing; Xiao, Wen-Jing; Chen, Jia-Rong; Yu, Xiao-Ye; Wang, Peng-Zi] Cent China Normal Univ, Key Lab Pesticide & Chem Biol, CCNU uOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Huanggang Normal Univ, Hubei Key Lab Proc & Applicat Catalyt Mat, Huanggang 438000, Hubei, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol, CCNU uOttawa Joint Res Ctr, Minist Educ,Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A photoredox-catalyzed iminyl radical-triggered C-C bond cleavage/addition/Kornblum oxidation cascade of cycloketone oxime esters and styrenes in DMSO is described. This three-component, one-pot procedure features mild conditions, a broad substrate scope, and high functional group tolerance, providing an efficient approach to access diversely functionalized ketonitriles.
期刊:
Chemical Communications,2018年54(58):8096-8099 ISSN:1359-7345
通讯作者:
Shi, De-Qing
作者机构:
[Zhao, Yu; Yao, Sheng; Xiao, Wen-Jing; Zhou, Quan-Quan; Zhang, Kai; Shi, De-Qing] 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] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China.
通讯机构:
[Shi, De-Qing] 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.
摘要:
Two photo-catalytic tandem alkyl radical addition/semipinacol rearrangement reactions of cycloalkanol-substituted styrenes with N-acyloxyphthalimides and O-acyl oximes have been documented. These protocols provide efficient access to functionalized cyclic ketones, and feature mild conditions (i.e., visible light irradiation, redox neutral and room temperature), broad substrate scope and excellent functional group tolerance.