Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to [alpha]-Trifluoromethyl Ketones

We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of [alpha]-CF3 ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3 radical from the triflyl group of enol triflate and subsequent additi...

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Veröffentlicht in:	Angewandte Chemie 2017-01, Vol.129 (5), p.1358
Hauptverfasser:	Su, Xiaolong, Huang, Honggui, Yuan, Yaofeng, Li, Yi
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Sprache:	ger
Schlagworte:	Chemistry
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creator	Su, Xiaolong Huang, Honggui Yuan, Yaofeng Li, Yi
description	We report an efficient oxidative radical desulfur-fragmentation and reconstruction of enol triflates for the synthesis of [alpha]-CF3 ketones. Preliminary mechanistic studies disclosed that oxidative fragmentation to release a CF3 radical from the triflyl group of enol triflate and subsequent addition of the CF3 radical to another enol triflate form the desired [alpha]-CF3 ketones. This method provides a new approach to [alpha]-CF3 ketones, featuring the utilization of catalytic amount of oxidants, broad substrate scope, and potential to control the regioselectivity.
doi_str_mv	10.1002/ange.201608507
format	Article
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subjects	Chemistry
title	Radical Desulfur-Fragmentation and Reconstruction of Enol Triflates: Facile Access to [alpha]-Trifluoromethyl Ketones
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