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Synlett 2022; 33(05): 495-501
DOI: 10.1055/a-1733-6073
DOI: 10.1055/a-1733-6073
letter
Palladium-Catalyzed Thiocarbonylations with Triisopropylsilyl Thioethers
This work was financially supported in part by JSPS KAKENHI Grant Number JP19H02725 and a Waseda University Grant for Special Research Projects.
Abstract
We have developed a palladium-catalyzed thiocarbonylation through the reaction of a σ-alkyl palladium intermediate with carbon monoxide and a triisopropylsilyl (TIPS) thioether. The use of CsF, (IPr)Pd(allyl)Cl [IPr =1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], CO, and a TIPS thioether in THF are key to obtaining alkyl and aryl thioesters in high yields. The yield of the palladium-catalyzed thiocarbonylation depended on the structure of the substrate; indoline-2-one derivatives were formed faster than indoline derivatives. The reactions of benzoyl and hydrocinnamoyl fluorides with TIPSSPh and CsF also gave the corresponding thioesters.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1733-6073.
- Supporting Information
Publication History
Received: 20 November 2021
Accepted after revision: 07 January 2022
Accepted Manuscript online:
07 January 2022
Article published online:
02 February 2022
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