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Synthesis 2023; 55(09): 1401-1409
DOI: 10.1055/a-2019-1532
special topic
Bürgenstock Special Section 2022 – Future Stars in Organic Chemistry

Photocatalytic Defluoroalkylation of Trifluoroacetates with Alkenes using 4-(Acetamido)thiophenol

Can Liu
a   Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Ni Shen
a   Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
,
Rui Shang  ∗
a   Department of Chemistry, University of Science and Technology of China, Hefei 230026, P. R. of China
b   Department of Chemistry, The University of Tokyo, Tokyo 113-0033, Japan
› Author AffiliationsThis work was financially supported by the University of Science and Technology of China (USTC; GG2065010002).
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Abstract

Under mild irradiation conditions using violet light-emitting diodes, a catalytic amount of a thiolate of N-(4-mercaptophenyl)pivalamide promotes monoselective defluoroalkylation of trifluoroacetates with a variety of aliphatic alkenes in the presence of a formate salt. The reactions allow facile and low-cost synthesis of valuable α,α-difluoro substituted aliphatic carboxylate esters under mild conditions, and demonstrate the dual-functional role of arenethiolates in photocatalysis as both a strong photoreductant in a redox cycle and a hydrogen-atom-transfer catalyst.

Key words

defluoroalkylation - trifluoroacetate - arenethiolate - dual function catalysts - photoredox catalysis - HAT catalysis

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2019-1532.
  • Supporting Information


Publication History

Received: 14 October 2022

Accepted after revision: 24 January 2023

Accepted Manuscript online:
24 January 2023

Article published online:
01 March 2023

© 2023. Thieme. All rights reserved

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