Synthesis of thionoesters

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A base-catalyzed transesterification enables a convenient synthesis of thionoesters in very good yields and short reaction times. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct.
J. J. Newton, R. Britton, C. M. Friesen, J. Org. Chem., 2018, 83, 12784-12792.

Selective addition reactions of various monothiocarboxylic acids to the ynamide MYTsA furnish α-thioacyloxyenamides. A subsequent transesterification with alcohols or thiols affords thionoesters and dithioesters, respectively. The method offers broad substrate scope, mild reaction conditions, and good yields.
C. Yao, J. Yang, X. Lu, S. Zhang, J. Zhao, Org. Lett., 2020, 22, 6628-6631.