Photoredox catalyzed reductive trifluoromethylation of imines via a radical umpolung strategy

被引：0

作者：

Paul, Hrishikesh ^{[1
]}

Das, Dibyangshu ^{[1
]}

Ariyan, S.K. ^{[1
]}

Pradhan, Suman ^{[1
]}

Chatterjee, Indranil ^{[1
]}

机构：

[1] Department of Chemistry, Indian Institute of Technology Ropar, Nangal Road, Punjab, Rupnagar,140001, India

来源：

Chemical Communications | 2024年 / 60卷 / 89期

关键词：

Synthesis; (chemical);

D O I：

10.1039/d4cc03897e

中图分类号：

O6 [化学]; TQ03 [化学反应过程]; TQ02 [化工过程（物理过程及物理化学过程）];

学科分类号：

0703 ; 081701 ; 081704 ;

摘要：

Visible light-induced radical umpolung chemistry is utilized to synthesize trifluoromethylated unnatural α-amino acid and amine derivatives. This approach utilizes photoredox catalysis to perform a single-electron-transfer reduction of imines generating a N-centred radical that eventually migrates to the C-centre followed by a radical-radical cross-coupling to deliver reductive trifluoromethylation products. © 2024 The Royal Society of Chemistry.

引用

页码：13016 / 13019

共 50 条

[21] Synthesis of 4-Difluoromethylquinolines by NHC-Catalyzed Umpolung of Imines
Patra, Atanu
Gelat, Fabien
Pannecoucke, Xavier
Poisson, Thomas
Besset, Tatiana
Biju, Akkattu T.
ORGANIC LETTERS, 2018, 20 (04) : 1086 - 1089
[22] Bronsted Base-Catalyzed Umpolung Intramolecular Cyclization of Alkynyl Imines
Kondoh, Azusa
Terada, Masahiro
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (16) : 3998 - 4001
[23] Palladium-catalyzed asymmetric umpolung allylation of imines with allylic alcohols
Qiao, Xiang-Chen
Zhu, Shou-Fei
Chen, Wang-Qiao
Zhou, Qi-Lin
TETRAHEDRON-ASYMMETRY, 2010, 21 (9-10) : 1216 - 1220
[24] Reductive alkylation of imines via asymmetric Cu-catalyzed addition of organozirconium reagents
Nemethova, Ivana
Vargova, Denisa
Mudrakova, Brigita
Filo, Juraj
Sebesta, Radovan
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 908
[25] Mechanistic insight into photoredox-catalyzed reductive deiodination
D'Amato, Erica M.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
[26] Copper-Catalyzed Synthesis of α-Trifluoromethylacrylates from Trifluoroborylacrylates via Stereoretentive Radical Trifluoromethylation
Jos, Swetha
Santos, Webster L.
ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (02) : 425 - 430
[27] Polarity Umpolung Strategy for the Radical Alkylation of Alkenes
Wei, Rongbiao
Bao, Hongli
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (06) : 1797 - 1799
[28] Polarity Umpolung Strategy for the Radical Alkylation of Alkenes
Liu, Jige
Wu, Shuo
Yu, Jiajia
Lu, Chenxi
Wu, Zhen
Wu, Xinxin
Xue, Xiao-Song
Zhu, Chen
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (21) : 8195 - 8202
[29] Photoredox-Catalyzed Benzylic Esterification via Radical-Polar Crossover
Maeda, Bumpei
Sakakibara, Yota
Murakami, Kei
Itami, Kenichiro
ORGANIC LETTERS, 2021, 23 (13) : 5113 - 5117
[30] Manganese-Dioxide-Catalyzed Trifluoromethylation and Azidation of Styrenyl Olefins via Radical Intermediates
Panday, Prabhakar
Garg, Parul
Singh, Anand
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (01) : 111 - 115

← 1 2 3 4 5 →