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Issue 7, 2016
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A general photoinduced electron transfer-directed chemoselective perfluoroalkylation of N,N-dialkylhydrazones

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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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Supplementary files

Article information


Submitted
14 Apr 2016
Accepted
09 May 2016
First published
10 May 2016

Org. Chem. Front., 2016,3, 841-845
Article type
Research Article

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

J. Xie, J. Li, T. Wurm, V. Weingand, H. Sung, F. Rominger, M. Rudolph and A. S. K. Hashmi, Org. Chem. Front., 2016, 3, 841
DOI: 10.1039/C6QO00158K

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