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Synthesis 2023; 55(09): 1401-1409
DOI: 10.1055/a-2019-1532
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
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 catalysisSupporting 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
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