Synthesis 2023; 55(09): 1401-1409
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
,
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 Affiliations This work was financially supported by the University of Science and Technology of China (USTC; GG2065010002).
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
© 2023. Thieme. All rights reserved
Georg Thieme Verlag KG
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