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Synthesis 2022; 54(06): 1661-1669
DOI: 10.1055/a-1671-6602
paper

A Concise Copper-Catalyzed Oxytrifluoromethylation of Allyl Alcohols

Longhui Chen
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Zequn Yang
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Qi Sun
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Minjie Guo
b   Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, P. R. of China
,
Xintong Feng
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Xiangyang Tang
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
,
Guangwei Wang  ∗
a   Tianjin Key Laboratory of Molecular Optoelectronic Science, Department of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. of China
› Author AffiliationsWe are grateful for the financial support from the Natural Science Foundation of Tianjin (19JCYBJC20200) and Tianjin University for support of this research.
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In deep memory of Dr. Ei-ichi Negishi.

Abstract

An efficient oxytrifluoromethylation of 1-aryl-substituted allyl alcohols has been developed using Togni’s reagent II as a trifluoromethylation reagent and copper(I) chloride as a catalyst. This reaction proceeded through a one-pot process of trifluoromethylation followed by nucleophilic attack of the vicinal hydroxyl group. This strategy features good diastereoselectivity and broad substrate scope, which provides a facile access to various 2-aryl-3-(2,2,2-trifluoroethyl)oxiranes.

Key words

oxytrifluoromethylation - allyl alcohols - CF3-substituted epoxides­ - Togni’s reagent - copper catalysis - 2-(2,2,2-trifluoroethyl)oxiranes­

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1671-6602.
  • Supporting Information


Publication History

Received: 18 September 2021

Accepted after revision: 18 October 2021

Accepted Manuscript online:
18 October 2021

Article published online:
30 November 2021

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