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Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.

ABSTRACT: We report herein an iron-catalyzed azidotrifluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo-radical instead of a carbocation species. Characterization of an active iron catalyst through X-ray crystallographic studies suggests that in situ generated, structurally novel iron-azide complexes promote the oxidant activation and selective azido-group transfer.

SUBMITTER: Zhu CL

PROVIDER: S-EPMC6010075 | biostudies-literature | 2018 Jun

REPOSITORIES: biostudies-literature

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Iron(II)-Catalyzed Azidotrifluoromethylation of Olefins and N-Heterocycles for Expedient Vicinal Trifluoromethyl Amine Synthesis.

Zhu Cheng-Liang CL Wang Cheng C Qin Qi-Xue QX Yruegas Sam S Martin Caleb D CD Xu Hao H

ACS catalysis 20180420 6

We report herein an iron-catalyzed azidotrifluoromethylation method for expedient vicinal trifluoromethyl primary-amine synthesis. This method is effective for a broad range of olefins and N-heterocycles, and it facilitates efficient synthesis of a wide variety of vicinal trifluoromethyl primary amines, including those that prove difficult to synthesize with existing approaches. Our preliminary mechanistic studies revealed that the catalyst-promoted azido-group transfer proceeds through a carbo- ...[more]

PMID: 29938121

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