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

被引：14

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

[21] Nickel-Catalyzed Reductive Cross-Coupling of Benzyl Halides with Aryl Halides
Zhang, Qingchen
Wang, Xuan
Qian, Qun
Gong, Hegui
SYNTHESIS-STUTTGART, 2016, 48 (17): : 2829 - 2836
[22] Nickel/photoredox dual-catalyzed reductive cross-coupling of aryl halides and aldehydes
Liu, Junjie
Chen, Yukun
Zhao, Hongping
Yuan, Weiming
ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (04) : 1205 - 1210
[23] Nickel-Catalyzed Desulfonylative Reductive Cross-Coupling of Aryl Sulfones with Aryl Bromides
Huang, Xinmiao
Tang, Ling
Song, Zhiyong
Jiang, Shuangshuang
Liu, Xianmao
Ma, Ming
Chen, Bo
Ma, Yuanhong
ORGANIC LETTERS, 2023, : 1198 - 1203
[24] Nickel-catalyzed reductive cross-coupling of difluoromethylated secondary alkyl bromides with organohalides
Liu, Bosheng
Dong, Jinxu
Wang, Hongyi
Chen, Jiaming
Liu, Shiwen
Xiong, Xiaodong
Yuan, Yanli
Zeng, Xiaojun
CHEMICAL COMMUNICATIONS, 2025, 61 (11) : 2357 - 2360
[25] Modular Access to Chiral ?-(Hetero)aryl Amines via Ni/Photoredox-Catalyzed Enantioselective Cross-Coupling
Shu, Xiaomin
Zhong, De
Lin, Yanmei
Qin, Xiao
Huo, Haohua
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (19) : 8797 - 8806
[26] Photoredox Catalysis in Nickel-Catalyzed Cross-Coupling
Cavalcanti, Livia N.
Molander, Gary A.
TOPICS IN CURRENT CHEMISTRY, 2016, 374 (04)
[27] Cross-Coupling of Gaseous Alkanes with (Hetero)Aryl Bromides via Dual Nickel/Photoredox Catalysis
Nair, Akshay M.
Martinez-Balart, Pol
Barbeira-Aran, Sergio
Fananas-Mastral, Martin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (02)
[28] Nickel/photoredox-catalyzed enantioselective arylation of α-chloro thioesters
Xing, Fei
Lin, Tingzhi
Ye, Yu
Wang, Yan-En
Cao, Xianzhong
Gao, Xueying
Zhang, Dongzhao
Kong, Lingfeng
Zhu, Xiyou
Xiong, Dan
Mao, Jianyou
CHEMICAL COMMUNICATIONS, 2023, 59 (89) : 13355 - 13358
[29] Amido Pincer Nickel Catalyzed Kumada Cross-Coupling of Aryl, Heteroaryl, and Vinyl Chlorides
Zhang, Xue-Qi
Wang, Zhong-Xia
SYNLETT, 2013, 24 (16) : 2081 - 2084
[30] Cobalt-Catalyzed Reductive Cross-Coupling Between Styryl and Benzyl Halides
Cai, Yingxiao
Benischke, Andreas D.
Knochel, Paul
Gosmini, Corinne
CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (02) : 250 - 253

← 1 2 3 4 5 →