摘要:
An unprecedented phototandem catalysis based on a single iridium photocatalyst has been successfully developed. This powerful strategy consists of two mechanistically distinct catalytic cycles, namely, photocatalytic energy transfer (ET) and single electron transfer (SET). The novel protocol allows a rapid and efficient construction of biologically and synthetically important 3-ester-3-hydroxy-2-oxindole derivatives from readily available diazoamides through a cyclization/aerobic oxidation sequence under very mild conditions.
期刊:
Chemical Communications,2015年51(17):3537-3540 ISSN:1359-7345
通讯作者:
Chen, Jia-Rong
作者机构:
[Lu, Liang-Qiu; Zhao, Quan-Qing; Deng, Qiao-Hui; Wei, Qiang; Xiao, Wen-Jing; Chen, Jia-Rong] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.;[Chen, Jia-Rong] 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:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A visible-light-induced photocatalytic oxytrifluoromethylation reaction of N-allylamides has been developed for the efficient synthesis of CF3-containing oxazolines and benzoxazines under mild reaction conditions.
作者机构:
[Qi, Ying-Hua; Feng, Bin; Xiao, Wen-Jing; Chen, Jia-Rong; Zhang, Hong; Chen, Li-Yan; Yu, Xiao-Ye] Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.;[Xiao, Wen-Jing] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A general and efficient Pd/sulfoxide-phosphine complex-catalyzed direct asymmetric N-allylic alkylation of indoles has been developed to allow for the preparation of various N-allylated indoles in generally good yields with excellent enantioselectivities. This catalytic system could also be extended to other N-containing heterocycles with good results.
作者机构:
[Chen,Jia-Rong; Lu,Liang-Qiu; Xiao,Wen-Jing] College of Chemistry,Central China Normal University
会议名称:
中国化学会全国第十二届有机合成化学学术研讨会
会议时间:
2015-01-01
会议地点:
中国广西桂林
会议论文集名称:
中国化学会全国第十二届有机合成化学学术研讨会论文摘要集
关键词:
heterocycles;photocatalysis;cycloaddition
摘要:
Substances containing carbocyclic and heterocyclic structures have attracted the broad interest of synthetic organic chemists because of their biological activities and fine chemical significance.1 The utilization of visible light photocatalytic strategies to construct these ring systems has received considerable attention in the past few years.The results of studies during this period have demonstrated that visible light photocatalytic reactions serve not only as practical methods to carry out simple organic transformations,they also are applicable to synthetic sequences designed to construct structurally complex heterocyclic substances.2 Since 2010,our group has been started to investigate the construction of heterocycles using visible light induced photocatalytic strategy.The method has been successfully applied to the synthesis of isoquino[2,1-a]pyrimidine,3a 4,5-dihydropyrazoles,3b pyrrole3c as well as many other biologically important ring structures.
通讯机构:
[Lu, Liang-Qiu] C;Cent China Normal Univ, Coll Chem, Minist Educ, Key Lab Pesticide & Chem Biol, Wuhan 430079, Peoples R China.
摘要:
A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.
期刊:
CHEMICAL REVIEWS,2015年115(11):5301-5365 ISSN:0009-2665
通讯作者:
Chen, Jia-Rong
作者机构:
[Lu, Liang-Qiu; Xiao, Wen-Jing; Chen, Jia-Rong; Hu, Xiao-Qiang] Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, Wuhan 430079, Hubei, Peoples R China.;[Chen, Jia-Rong] 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:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticide & Chem Biol, Minist Educ, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
The development of new strategies and chemical reactions continues to be a major focus of research efforts in the modern synthetic organic community. Of the various types of reactions that have been discovered over the past 90 years, cyclization and cycloaddition reactions have been established as the most synthetically useful and theoretically and mechanistically investigated transformations. Carbon monoxide (CO) is an important type of C1 feedstock, and transition metal-catalyzed carbonylative cycloadditions have provided tremendous methods for an extensive variety of diversely functionalized carbocyclic and heterocyclic carbonyl compounds.
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Coll Chem, Key Lab Pesticides & Chem Biol, Minist Educ, Wuhan 430079, Peoples R China.
摘要:
A general visible light induced photoredox-catalyzed radical trifluoromethylation/cyclization cascade of β-aryl-β,γ-unsaturated hydrazones and oximes is described. The protocol enables an efficient access to various densely functionalized and biologically important CF3-containing dihydropyrazoles and isoxazolines with generally high yields.
摘要:
<正>Indoles and their derivatives are a family of privileged heterocyclic structures commonly found in a number of natural products and many biologically active molecules.~1 Among them,2-substituted in
通讯机构:
[Chen, Jia-Rong] C;Cent China Normal Univ, Key Lab Pesticide & Chem Biol Educ, Minist Coll Chem, 152 Luoyu Rd, Wuhan 430079, Hubei, Peoples R China.
摘要:
A new type of chiral sulfoxide-phosphine ligands have been developed by a rational combination of two privileged scaffolds for Pd-catalyzed asymmetric allylic alkylation reactions. Under optimized conditions, generally high yields (up to 97%) and excellent enantioselectivities (up to >99% ee) were obtained.
摘要:
Through nearly 50 years of development, sulphur ylides have been established as versatile and powerful reagents for the construction of carbocycles and heterocycles. Despite advances, two important and yet elusive bottlenecks continue to inhibit the advancement of this chemistry: a limited number of reagents with polar groups to react with sulphur ylides, and the wide utilization of chiral auxiliaries or substrates to achieve asymmetric cycloaddition processes in the majority of known reports. Herein, we apply an asymmetric palladium catalysis strategy to the chemistry of sulphur ylides to address these two fundamental problems. We thus achieve an unprecedented decarboxylation-cycloaddition sequence of cyclic allylic esters with sulphur ylides through the enantioselective trapping of Pd-stabilized zwitterionic intermediates by the ylides. As a result, a series of biologically and synthetically important 3-vinyl indolines are rapidly assembled with a high reaction efficiency and stereoselectivity.