AgSCF3-mediated trifluoromethylthiolation of α,α-diaryl allylic alcohols via radical neophyl rearrangement

Kai Liu; Qiao Jin; Shuang Chen; Pei Nian Liu

doi:10.1039/C6RA25378D

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AgSCF₃-mediated trifluoromethylthiolation of α,α-diaryl allylic alcohols via radical neophyl rearrangement†

Kai Liu,^a Qiao Jin,^a Shuang Chen^a and Pei Nian Liu*^a

Author affiliations

* Corresponding authors

^a Shanghai Key Laboratory of Functional Materials Chemistry, Key Lab for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Meilong Road 130, Shanghai, China
E-mail: liupn@ecust.edu.cn

Abstract

A novel example of AgSCF₃-mediated oxidative radical trifluoromethylthiolation of α,α-diaryl allylic alcohols is presented, producing various α-aryl-β-trifluoromethylthiolated carbonyl ketones via radical neophyl rearrangement under mild conditions. This protocol involves formation of C(Ar)–C(sp³) and C(sp³)–S bonds in one step and tolerates a wide range of symmetrical and nonsymmetrical α,α-diaryl allylic alcohols.

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Article information

DOI: https://doi.org/10.1039/C6RA25378D
Article type: Paper
Submitted: 17 Oct 2016
Accepted: 21 Nov 2016
First published: 05 Jan 2017
This article is Open Access

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RSC Adv., 2017,7, 1546-1552

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AgSCF₃-mediated trifluoromethylthiolation of α,α-diaryl allylic alcohols via radical neophyl rearrangement

K. Liu, Q. Jin, S. Chen and P. N. Liu, RSC Adv., 2017, 7, 1546 DOI: 10.1039/C6RA25378D

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