Cyano migration-mediated radical-polar crossover cyclopropanation

被引:0
作者
Ziqiang Wang [1 ,2 ]
Yasu Chen [2 ]
Jie Li [1 ]
Chen Zhu [1 ,2 ]
机构
[1] Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science,Soochow University
[2] Frontiers Science Center for Transformative Molecules, Zhangjiang Institute for Advanced Study and Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, Shanghai Jiao Tong University
关键词
D O I
暂无
中图分类号
O621.251 [];
学科分类号
070303 ; 081704 ;
摘要
We report a novel cyano migration-mediated radical-polar crossover process, whereby both the sulfonylcyanation of aliphatic alkenes and the formation of cyclopropanes are concurrently achieved. This transformation yields a diverse array of multisubstituted cyclopropanes under mild photocatalytic conditions. Mechanistic studies elucidate that the reaction proceeds via intramolecular nucleophilic substitution, leading to the formation of the cyclopropane derivatives.
引用
收藏
页码:241 / 248
页数:8
相关论文
共 50 条
[11]   TETRATHIAFULVALENE AS A CATALYST FOR RADICAL-POLAR CROSSOVER REACTIONS [J].
LAMPARD, C ;
MURPHY, JA ;
ROOME, SJ ;
LEWIS, N .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 :102-ORGN
[12]   Catalytic Asymmetric Radical-Polar Crossover Hydroalkoxylation [J].
Discolo, Christopher A. ;
Touney, Eric E. ;
Pronin, Sergey V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (44) :17527-17532
[13]   Photoinduced radical-polar crossover cyclization reactions [J].
Zhu, Zhiming ;
Zhang, Yongxin ;
Li, Ziyang ;
Shu, Chao .
CHEM CATALYSIS, 2024, 4 (05)
[14]   Mechanism Switch Between Radical-Polar Crossover and Radical Buffering [J].
Xu, Minghao ;
Li, Yan-Bo ;
Wang, Huamin ;
Glorius, Frank ;
Qi, Xiaotian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (21)
[15]   Synthesis of functionalised indolines by radical-polar crossover reactions [J].
Murphy, JA ;
Rasheed, F ;
Gastaldi, S ;
Ravishanker, T ;
Lewis, N .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (10) :1549-1558
[16]   Catalytic Radical-Polar Crossover Reactions of Allylic Alcohols [J].
Touney, Eric E. ;
Foy, Nicholas J. ;
Pronin, Sergey V. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (49) :16982-16987
[17]   Electrocatalytic Radical-Polar Crossover Hydroetherification of Alkenes with Phenols [J].
Park, Steve H. ;
Jang, Jieun ;
Shin, Kwangmin ;
Kim, Hyunwoo .
ACS CATALYSIS, 2022, 12 (17) :10572-10580
[18]   Photoredox-Catalyzed Cyclopropanation of 1,1-Disubstituted Alkenes via Radical-Polar Crossover Process [J].
Luo, Wenping ;
Yang, Yi ;
Fang, Yewen ;
Zhang, Xinxin ;
Jin, Xiaoping ;
Zhao, Guicai ;
Zhang, Li ;
Li, Yan ;
Zhou, Wanli ;
Xia, Tingting ;
Chen, Bin .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (18) :4215-4221
[19]   Termination of radical-polar crossover reactions by intramolecular nucleophiles [J].
Murphy, JA ;
Rasheed, F ;
Roome, SJ ;
Lewis, N .
CHEMICAL COMMUNICATIONS, 1996, (06) :737-738
[20]   Enantioselective Radical-Polar Crossover Reactions of Indanonecarboxamides with Alkenes [J].
Zhang, Xiying ;
Wu, Wangbin ;
Cao, Weidi ;
Yu, Han ;
Xu, Xi ;
Liu, Xiaohua ;
Feng, Xiaoming .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (12) :4846-4850