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Angewandte Chemie International Edition

Angewandte Chemie International Edition

IF: 16.1
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Hydrotrifluoromethylthiolation of Unactivated Alkenes and Alkynes with Trifluoromethanesulfonic Anhydride through Deoxygenative Reduction and Photoredox Radical Processes

Published:14 October 2019 DOI: 10.1002/anie.201911323 PMID: 31612551
Yao Ouyang, Dr. Xiu-Hua Xu, Prof.?Dr. Feng-Ling Qing

Abstract

An ongoing challenge in trifluoromethylthiolation reactions is the use of less expensive and easily available trifluoromethylthio sources. Herein, we disclose an unprecedented usage of trifluoromethanesulfonic anhydride (Tf2O) as a radical trifluoromethylthiolating reagent. Hydrotrifluoromethylthiolation of unactivated alkenes and alkynes with Tf2O in the presence of PMePh2 and H2O under visible-light photoredox catalysis gave the addition products. The trifluoromethylthio radical (.SCF3) was first formed from Tf2O through a photoredox radical processes and deoxygenative reduction of PMePh2, and H2O serves as the H-atom donor for the hydrotrifluoromethylthiolation reaction. This reaction provides a new strategy for radical trifluoromethylthiolation.

Substances (3)

Related products
Procduct Name CAS Molecular Formula Supplier Price
Trifluoromethanesulfonic anhydride 358-23-6 C2F6O5S2 699 suppliers $10.00-$6920.07
2-Methoxyethanol 109-86-4 C3H8O2 590 suppliers $11.00-$6520.00
Scandium trifluoride 13709-47-2 F3Sc 111 suppliers $35.00-$1304.36

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