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

[11] Dual Nickel- and Photoredox-Catalyzed Reductive Cross-Coupling of Aryl Halides with Dichloromethane via a Radical Process
Xu, Wenhao
Zheng, Purui
Xu, Tao
ORGANIC LETTERS, 2020, 22 (21) : 8643 - 8647
[12] Trifluoromethylation of heterocycles via visible light photoredox catalysis
Iqbal, Naeem
Choi, Sungkyu
Ko, Euna
Cho, Eun Jin
TETRAHEDRON LETTERS, 2012, 53 (15) : 2005 - 2008
[13] Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay
Wang, Shun
Cheng, Bei-Yi
Srsen, Matea
Koenig, Burkhard
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) : 7524 - 7531
[14] TTMPP-catalyzed trifluoromethylation of carbonyl compounds and imines with trifluoromethylsilane
Matsukawa, Satoru
Saijo, Marina
TETRAHEDRON LETTERS, 2008, 49 (31) : 4655 - 4657
[15] Copper(II)-catalyzed trifluoromethylation of N-aryl imines
Zhang, Yong-Qiang
Liu, Ji-Dan
Xu, Hao
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (37) : 6242 - 6245
[16] An Organocatalytic Biomimetic Strategy Paves the Way for the Asymmetric Umpolung of Imines
Waser, Mario
Novacek, Johanna
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (48) : 14228 - 14231
[17] Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis
Xu, Pin
Fan, Wenzheng
Chen, Pinhong
Liu, Guosheng
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (30) : 13468 - 13474
[18] Umpolung synthesis of branched α-functionalized amines from imines via photocatalytic three-component reductive coupling reactions
de Arriba, Angel L. Fuentes
Urbitsch, Felix
Dixon, Darren J.
CHEMICAL COMMUNICATIONS, 2016, 52 (100) : 14434 - 14437
[19] Enantioselective Radical Functionalization of Imines and Iminium Intermediates via Visible-Light Photoredox Catalysis
Zhao, Jia-Jia
Zhang, Hong-Hao
Yu, Shouyun
SYNTHESIS-STUTTGART, 2021, 53 (10): : 1706 - 1718
[20] Acetic acid-promoted photoredox catalyzed trifluoromethylation of aldehyde hydrazones
Aryal, Puspa
Rafiu, Raheemat
Reddy, V. Prakash
JOURNAL OF FLUORINE CHEMISTRY, 2022, 261

← 1 2 3 4 5 →