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. 2016 Aug 19;81(16):7301-7.
doi: 10.1021/acs.joc.6b01031. Epub 2016 Jun 13.

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

Cecilia Bottecchia  1 , Xiao-Jing Wei  1 , Koen P L Kuijpers  1 , Volker Hessel  1 , Timothy Noël  1
Affiliations

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

Cecilia Bottecchia et al. J Org Chem. .

Abstract

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.

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