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Synthesis 2023; 55(12): 1844-1854
DOI: 10.1055/a-2042-3720
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Synthesis of 1-(Trifluoromethyl)alkenes through Transition-Metal-Catalyzed Alkylation and Arylation of 1-Chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233zd)

Wei Zhou
a   College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China
,
Qing-Wei Zhao
a   College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China
,
Yun-Cheng Luo
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China
,
Xingang Zhang∗
a   College of Chemistry, Henan Institute of Advanced Technology, Zhengzhou University, Zhengzhou 450001, P. R. of China
b   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, P. R. of China
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (21991122), the National Key Research and Development Program of China (2021YFF0701700), and the Science and Technology Commission of Shanghai Municipality (21ZR147660).
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Abstract

The synthesis of 1-(trifluoromethyl)alkenes through nickel-catalyzed alkylation/arylation of 1-chloro-3,3,3-trifluoroprop-1-ene (HCFO-1233zd) with alkyl/aryl zinc reagents and cobalt-catalyzed reductive cross-coupling between HCFO-1233zd and aryl bromides has been developed. These approaches feature broad substrate scope, high functional group tolerance, and the use of industrial feedstocks and low-cost nickel/cobalt catalysts, providing facile routes to access 1-(trifluoromethyl)alkenes. Diverse transformations of the resulting 1-(trifluoromethyl)alkenes demonstrated the synthetic utility of the current approaches.

Key words

HCFO-1233zd - nickel catalysis - cobalt catalysis - cross-coupling - 1-(trifluoromethyl)alkene

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2042-3720.
  • Supporting Information


Publication History

Received: 13 December 2022

Accepted after revision: 24 February 2023

Accepted Manuscript online:
24 February 2023

Article published online:
23 March 2023

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