Journal
ORGANIC LETTERS
Volume 21, Issue 23, Pages 9521-9526Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b03701
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Funding
- KY [2060000119]
- National Key R&D Program of China [2018YFB1501600, 2017YFA0303502]
- Strategic Priority Research Program of CAS [XDB20000000, XDA21060101]
- HCPST [2017FXZY001]
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Oxalic acid monothioester (OAM), an easily accessible and storable reagent, was reported herein as a thioester synthetic equivalent for palladium-catalyzed decarboxylative thiocarbonylation of organohalides and hydrothiocarbonylation of unsaturated carbon-carbon bonds at room temperature with high chemo- and regioselectivity. The reaction is applicable to the synthesis of cysteine-derived thioesters, thus allowing chemical modification of cysteine-containing peptides. Decarboxylation of OAM proceeds through oxidative addition of Pd(0) to the acyl-S bond, which accounts for the very mild reaction conditions.
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