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Photocatalytic Reductive Fluoroalkylation of Nitrones

Vyacheslav I. Supranovich, Vitalij V. Levin, Marina I. Struchkova and Alexander D. Dilman*

*N. D. Zelinsky Institute of Organic Chemistry, Leninsky prosp. 47, 119991 Moscow, Russian Federation, Email: adil25mail.ru

V. I. Supranovich, V. V. Levin, M. I. Struchkova, A. D. Dilman, Org. Lett., 2018, 20, 840-843.

DOI: 10.1021/acs.orglett.7b03987 (free Supporting Information)



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Abstract

An iridium photocatalyst enables the addition of fluorinated groups to nitrones using ascorbic acid as a stoichiometric reducing agent. Partially fluorinated alkyl iodides can also be effectively used. The resulting hydroxylamines can be readily converted to valuable fluorinated amines by reduction with zinc.

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proposed mechanism



Key Words

trifluoromethylation, perfluoromethylation, ascorbic acid, photochemistry


ID: J54-Y2018