Catalytic Asymmetric Reductive Azaarylation of Olefins via Enantioselective Radical Coupling

被引:60
作者
Li, Yajuan [1 ]
Han, Cuijie [1 ]
Wang, Yanyan [2 ]
Huang, Xin [1 ]
Zhao, Xiaowei [1 ]
Qiao, Baokun [1 ]
Jiang, Zhiyong [1 ,2 ]
机构
[1] Henan Univ, Int S&T Cooperat Base Chiral Chem, Kaifeng 475004, Henan, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453007, Henan, Peoples R China
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
C-H BONDS; PHOTOREDOX CATALYSIS; ELECTRON-TRANSFER; ALPHA-BENZYLATION; DIRECT ARYLATION; METAL-COMPLEXES; BRONSTED ACID; KETONES; ACTIVATION; AMINO;
D O I
10.1021/jacs.2c01458
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Visible-light-driven photocatalytic reductive azaarylation has been widely used to construct the important imine-containing azaarene derivatives. In addition to the direct use of various commercially available cyanoazaarenes as feedstocks, thesynthetic advantages include precise regioselectivity, high efficiency, mild reaction conditions, and good functional group tolerance.However, although many efficient reductive azaarylation methods have been established, the example of an enantioselective manneris still unmet, which most likely can be ascribed to the highly reactive radical coupling as the key step of forming stereocenters.Exploring the feasibility of enantiocontrol thus constitutes an attractive but highly challenging task. Here, we demonstrate that chiralhydrogen-bonding/photosensitizer catalysis is a viable platform as it enables the realization of thefirst enantioselective manifold. Avariety of acyclic and cyclic enones as the reaction partners are compatible with the dual catalyst system, leading to a wide array ofvaluable enantioenriched azaarene variants with high yields and ees. Regulating the types of chiral catalysts represents one of theimportant manners to success, in which several readily accessibleCinchonaalkaloid-derived bifunctional catalysts are introduced in asymmetric photochemical reactions.
引用
收藏
页码:7805 / 7814
页数:10
相关论文
共 86 条
[1]   Visible Light Photocatalysis for the Generation and Use of Reactive Azolyl and Polyfluoroaryl Intermediates [J].
Arora, Amandeep ;
Weaver, Jimmie D. .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) :2273-2283
[2]   C=N-Containing Azaarenes as Activating Groups in Enantioselective Catalysis [J].
Best, Daniel ;
Lam, Hon Wai .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (03) :831-845
[3]   RETRACTED: Reductive Arylation of Arylidene Malonates Using Photoredox Catalysis (Retracted Article) [J].
Betori, Rick C. ;
Scheidt, Karl A. .
ACS CATALYSIS, 2019, 9 (11) :10350-+
[4]   Construction and Functionalization of Heteroarenes by Use of Photoredox Catalysis [J].
Boubertakh, Oualid ;
Goddard, Jean-Philippe .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (15) :2072-2084
[5]   Enantioselective Catalysis of Photochemical Reactions [J].
Brimioulle, Richard ;
Lenhart, Dominik ;
Maturi, Mark M. ;
Bach, Thorsten .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :3872-3890
[6]   Catalytic Enantioselective Addition of Prochiral Radicals to Vinylpyridines [J].
Cao, Kangning ;
Tan, Siu Min ;
Lee, Richmond ;
Yang, Songwei ;
Jia, Hongshao ;
Zhao, Xiaowei ;
Qiao, Baokun ;
Jiang, Zhiyong .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (13) :5437-5443
[7]   Photochemical Strategies for Carbon-Heteroatom Bond Formation [J].
Cavedon, Cristian ;
Seeberger, Peter H. ;
Pieber, Bartholomaeus .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (10) :1379-1392
[8]   Asymmetric Hydroaminoalkylation of Alkenylazaarenes via Cooperative Photoredox and Chiral Hydrogen-Bonding Catalysis [J].
Chai, Xiangpei ;
Hu, Xinheng ;
Zhao, Xiaowei ;
Yin, Yanli ;
Cao, Shanshan ;
Jiang, Zhiyong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (10)
[9]   Metal-complexes of optically active amino- and imino-based pyridine ligands in asymmetric catalysis [J].
Chelucci, Giorgio .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (11-12) :1887-1932
[10]   Intermolecular, redox-neutral azidoarylation of alkenes via photoredox catalysis [J].
Chen, Jian ;
Zhu, Shengqing ;
Qin, Jian ;
Chu, Lingling .
CHEMICAL COMMUNICATIONS, 2019, 55 (16) :2336-2339