Practical photocatalytic trifluoromethylation and hydrotrifluoromethylation of styrenes in batch and flow

Natan J.W. Straathof; Sten E. Cramer; Volker Hessel; Timothy Noël

doi:10.1002/anie.201608297

Practical photocatalytic trifluoromethylation and hydrotrifluoromethylation of styrenes in batch and flow

Natan J.W. Straathof
, Sten E. Cramer
, Volker Hessel
, Timothy Noël

Research output: Contribution to journal › Article › Academic › peer-review

194 Citations (SciVal)

803 Downloads (Pure)

Abstract

Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)₃, visible light and inexpensive CF₃I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.

Original language	English
Pages (from-to)	15549-15553
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	55
Issue number	50
DOIs	https://doi.org/10.1002/anie.201608297
Publication status	Published - 1 Jan 2016

Keywords

continuous flow
hydrotrifluoromethylation
microreactor
photoredox catalysis
trifluoromethylation

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10.1002/anie.201608297

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AU - Noël, Timothy

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AB - Styrenes represent a challenging class of substrates for current radical trifluoromethylation and hydrotrifluoromethylation methods due to a myriad of potential side reactions. Herein, we describe the development of mild, selective and broadly applicable photocatalytic trifluoromethylation and hydrotrifluoromethylation protocols for these challenging substrates. The methods use fac-Ir(ppy)3, visible light and inexpensive CF3I and can be applied to a diverse set of vinylarene substrates. The use of continuous-flow photochemical reaction conditions allowed to reduce the reaction time and increase the reaction selectivity.

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KW - photoredox catalysis

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Practical photocatalytic trifluoromethylation and hydrotrifluoromethylation of styrenes in batch and flow

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