Visible light-induced trifluoromethylation and perfluoroalkylation of cysteine residues in batch and continuous flow

Article

Bottecchia, C., Wei, X.-J., Kuijpers, K.P.L., Hessel, V. & Noël, T. (2016). Visible light-induced trifluoromethylation and perfluoroalkylation of cysteine residues in batch and continuous flow. Journal of Organic Chemistry, 81(16), 7301-7307. In Scopus Cited 7 times.

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Abstract

 

We report a visible light-induced trifluoromethylation and perfluoroalkylation for cysteine conjugation using Ru(bpy)32+ 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.