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

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