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

C. Bottecchia, X.-J. Wei, K.P.L. Kuijpers, V. Hessel, T. Noël

Research output: Contribution to journalArticleAcademicpeer-review

35 Citations (Scopus)
2 Downloads (Pure)

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.
Original languageEnglish
Pages (from-to)7301-7307
JournalJournal of Organic Chemistry
Volume81
Issue number16
DOIs
Publication statusPublished - 19 Aug 2016

Fingerprint

Dive into the research topics of 'Visible light-induced trifluoromethylation and perfluoroalkylation of cysteine residues in batch and continuous flow'. Together they form a unique fingerprint.

Cite this