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

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• 作者：Cecilia Bottecchia ; Xiao-Jing Wei ; Koen P. L. Kuijpers ; Volker Hessel ; Timothy Noël
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：August 19, 2016
• 年：2016
• 卷：81
• 期：16
• 页码：7301-7307
• 全文大小：470K
• 年卷期：0
• ISSN：1520-6904

文摘

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