Catalytic Radical Intramolecular Aminoperfluoroalkylation and Aminodifluoromethylation of Unactivated Alkenes with Fluoro­alkylsulfonyl Chlorides

Published as part of the Special Topic Modern Cyclization Strategies in Synthesis

Abstract

The Cu(I)/phosphoric acid (PA) dual-catalyzed radical aminoperfluoroalkylation and aminodifluoromethylation of alkenes with commercially available fluoroalkylsulfonyl chlorides as the radical source is described. Functionalized α-tertiary pyrrolidines bearing four types of fluoroalkyl groups are obtained with moderate to excellent yields. The introduction of a Cu(I)/phosphoric acid dual catalytic system and the use of silver carbonate as a key additive to inhibit the side hydroamination reaction caused by the in situ generated HCl are crucial for the transformation.

Key words

fluoroalkylsulfonyl chlorides - aminodifluoromethylation - aminoperfluoroalkylation - radical - dual catalytic - pyrrolidines - unactivated alkenes

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