Visible Light-Induced Trifluoromethylation and Perfluoroalkylation of Cysteine Residues in Batch and Continuous Flow

被引：54

作者：

Bottecchia, Cecilia ^{[1
]}

Wei, Xiao-Jing ^{[1
]}

Kuijpers, Koen P. L. ^{[1
]}

Hessel, Volker ^{[1
]}

Noel, Timothy ^{[1
]}

机构：

[1] Eindhoven Univ Technol, Dept Chem Engn & Chem, Micro Flow Chem & Proc Technol, Dolech 2, NL-5612 AZ Eindhoven, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 16期

关键词：

FLUORINATED AMINO-ACIDS; PHOTOREDOX CATALYSIS; FLUOROUS SYNTHESIS; F-19; NMR; PROTEINS; PHASE; MILD; PHOTOCHEMISTRY; GENERATION; CHEMISTRY;

D O I：

10.1021/acs.joc.6b01031

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report a-visible light-induced trifluoromethylation and perfluoroalkylation for cysteine conjugation using Ru(bpy)(3)(2+) as photocatalyst and inexpensive RFI as coupling partner. The protocol allows the introduction of a variety of perfluoro alkyl groups (C1-C10) and a CF2COOEt moiety. The reaction is high yielding (56-94% yield) and fast (2 h in batch, 12 examples). Process intensification in a photomicroreactor accelerated the reaction (5 min reaction time) and increased the yields (8 examples), Quantum yield investigations support a radical chain mechanism.

引用

页码：7301 / 7307

页数：7

共 50 条

[1] Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero) aromatics in batch and continuous flow
Lefebvre, Quentin
Hoffmann, Norbert
Rueping, Magnus
CHEMICAL COMMUNICATIONS, 2016, 52 (12) : 2493 - 2496
[2] Visible light-induced phosphine-catalyzed perfluoroalkylation of indoles
Gao, Xiuhui
Pan, Xuling
Wang, Peiyi
Jin, Zhichao
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (21) : 5790 - 5797
[3] α-Trifluoromethylation of ketones by metal-free visible light photoredox catalysis: Batch and continuous flow strategies
Kappe, C. Oliver
Cantillo, David
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
[4] Visible-Light-Induced Trifluoromethylation of Highly Functionalized Arenes and Heteroarenes in Continuous Flow
Abdiaj, Irini
Bottecchia, Cecilia
Alcazar, Jesus
Noel, Timothy
SYNTHESIS-STUTTGART, 2017, 49 (22): : 4978 - 4985
[5] Visible-light-mediated direct perfluoroalkylation and trifluoromethylation of free anilines
He, Chun-Yang
Gu, Ji-Wei
Zhang, Xingang
TETRAHEDRON LETTERS, 2017, 58 (41) : 3939 - 3941
[6] Visible light-induced iniferter polymerization of methacrylates enhanced by continuous flow
Rubens, Maarten
Latsrisaeng, Phanumat
Junkers, Tanja
POLYMER CHEMISTRY, 2017, 8 (42) : 6496 - 6505
[7] Visible-Light-Induced Trifluoromethylation/Cyclization of 1,7-Enynes in Continuous Flow
Zhuang, Kaiqiang
Cui, Yusheng
Yuan, Xin
Qin, Longzhou
Sun, Qi
Duan, Xiu
Chen, Lin
Zhang, Xinpeng
Qiu, Jiangkai
Guo, Kai
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2020, 8 (31): : 11729 - 11736
[8] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
Straathof, Natan J. W.
van Osch, Dannie J. G. P.
Schouten, Arian
Wang, Xiao
Schouten, Jaap C.
Hessel, Volker
Noel, Timothy
JOURNAL OF FLOW CHEMISTRY, 2014, 4 (01) : 12 - 17
[9] Visible Light Photocatalytic Metal-Free Perfluoroalkylation of Heteroarenes in Continuous Flow
Natan J. W. Straathof
Dannie J. G. P. van Osch
Arian Schouten
Xiao Wang
Jaap C. Schouten
Volker Hessel
Timoth Noël
Journal of Flow Chemistry, 2014, 4 : 12 - 17
[10] Catalyst-free and visible light promoted trifluoromethylation and perfluoroalkylation of uracils and cytosines
Huang, Yang
Lei, Yun-Yun
Zhao, Liang
Gu, Jiwei
Yao, Qiuli
Wang, Ze
Li, Xiao-Fei
Zhang, Xingang
He, Chun-Yang
CHEMICAL COMMUNICATIONS, 2018, 54 (97) : 13662 - 13665

← 1 2 3 4 5 →