Nickel/Photoredox-Catalyzed Enantioselective Reductive Cross-Coupling between Vinyl Bromides and Benzyl Chlorides

被引：13

作者：

Lu, Qianqian ^{[1
]}

Guan, Haixing ^{[1
,2
]}

Wang, Yan-En ^{[3
]}

Xiong, Dan ^{[1
]}

Lin, Tingzhi ^{[1
]}

Xue, Fei ^{[2
]}

Mao, Jianyou ^{[1
]}

机构：

[1] Nanjing Tech Univ, Sch Chem & Mol Engn, Inst Adv Synth, Tech Inst Fluorochem TIF, Nanjing 211816, Peoples R China

[2] Nanjing Forestry Univ, Inst Mat Phys & Chem, Coll Sci, Nanjing 210037, Peoples R China

[3] Hebei Agr Univ, Coll Sci, Baoding 071000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 12期

基金：

中国国家自然科学基金;

关键词：

ASYMMETRIC SUZUKI-MIYAURA; ALPHA-BROMO ESTERS; ARYL BROMIDES; NEGISHI ARYLATIONS; NICKEL; HALIDES; MECHANISMS; LIGHT;

D O I：

10.1021/acs.joc.2c00707

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A visible-light-promoted nickel/photoredox-catalyzed reductive cross-coupling reaction between vinyl bromides and benzyl chlorides is reported. A diverse array of enantioenriched allylic centers containing products could be achieved in good yields (up to 90%) and high enantioselectivities (up to 95% ee). The mechanistic studies show that this reductive cross-coupling involves a radical pathway.

引用

页码：8048 / 8058

页数：11

共 50 条

[1] Dual nickel- and photoredox-catalyzed reductive cross-coupling of aryl vinyl halides and unactivated tertiary alkyl bromides
Yu, Weijie
Chen, Long
Tao, Jiasi
Wang, Tao
Fu, Junkai
CHEMICAL COMMUNICATIONS, 2019, 55 (42) : 5918 - 5921
[2] Enantioselective Reductive Cross-Coupling of Aryl/Alkenyl Bromides with Benzylic Chlorides via Photoredox/Biimidazoline Nickel Dual Catalysis
Li, Tongtong
Cheng, Xiaokai
Lu, Jiamin
Wang, Huifeng
Fang, Qun
Lu, Zhan
CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (09) : 1033 - 1038
[3] Nickel-Catalyzed Asymmetric Reductive Cross-Coupling Between Vinyl and Benzyl Electrophiles
Cherney, Alan H.
Reisman, Sarah E.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (41) : 14365 - 14368
[4] Nickel/Photoredox-Catalyzed Asymmetric Reductive Cross-Coupling of Racemic α-Chloro Esters with Aryl Iodides
Guan, Haixing
Zhang, Qianwen
Walsh, Patrick J.
Mao, Jianyou
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) : 5172 - 5177
[5] Nickel-catalyzed cross-coupling of diphenylphosphine with vinyl bromides and chlorides as a route to diphenylvinylphosphines
Shulyupin, MO
Chirkov, EA
Kazankova, MA
Beletskaya, LP
SYNLETT, 2005, (04) : 658 - 660
[6] Dual Nickel- and Photoredox-Catalyzed Reductive Cross-Coupling to Access Chiral Trifluoromethylated Alkanes
Zhou, Pan
Li, Xinxuan
Wang, Dong
Xu, Tao
ORGANIC LETTERS, 2021, 23 (12) : 4683 - 4687
[7] Nickel-Catalyzed Reductive Cross-Coupling of Vinyl Bromides with Unactivated Alkyl Halides
Gu, Jun
Qiu, Canbin
Lu, Wenbin
Qian, Qun
Lin, Kunhua
Gong, Hegui
SYNTHESIS-STUTTGART, 2017, 49 (08): : 1867 - 1873
[8] Nickel-Catalyzed Enantioselective Electrochemical Reductive Cross-Coupling of Aryl Aziridines with Alkenyl Bromides
Hu, Xia
Cheng-Sanchez, Ivan
Cuesta-Galisteo, Sergio
Nevado, Cristina
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (11) : 6270 - 6279
[9] Cobalt-Catalyzed Reductive Cross-Coupling Between Benzyl Chlorides and Aryl Halides
Pal, Suman
Chowdhury, Sushobhan
Rozwadowski, Elodie
Auffrant, Audrey
Gosmini, Corinne
ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (15) : 2431 - 2435
[10] Nickel-Catalyzed Enantioselective Cross-Coupling of N-Hydroxyphthalimide Esters with Vinyl Bromides
Suzuki, Naoyuki
Hofstra, Julie L.
Poremba, Kelsey E.
Reisman, Sarah E.
ORGANIC LETTERS, 2017, 19 (08) : 2150 - 2153

← 1 2 3 4 5 →