A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones??

Organic Chemistry Frontiers Pub Date: 2016-05-10 DOI: 10.1039/C6QO00158K

Abstract

A selective, practical and general incorporation of fluoroalkyl groups into organic frameworks is of great interest for synthesis. Herein we report the first metal-free, initiator-free, and general photochemical perfluoroalkylation of a variety of N,N-dialkylhydrazones at room temperature in the absence of any external photocatalyst. It constitutes an important advance in perfluoroalkyl radical addition to C[double bond, length as m-dash]N π bonds for the synthesis of hydrazones instead of amines. Affordable and easily available perfluoroalkyl iodides serve as effective precursors. The excellent regio-, stereo- and chemoselectivity as well as the broad substrate scope make this a very promising synthetic tool.

Graphical abstract: A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones
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