40669-39-4Relevant academic research and scientific papers
An efficient and straightforward approach for accessing thionoesters: Via palladium-catalyzed C-N cleavage of thioamides
Liu, Yinbo,Mo, Xiaofeng,Majeed, Irfan,Zhang, Mei,Wang, Hui,Zeng, Zhuo
, p. 1532 - 1537 (2022/03/01)
We report for the first time the coupling of activated thioamides with alcohols to efficiently form thionoesters via a palladium-catalyzed C-N cleavage strategy. The new approach employs thioamides as a thioacylating reagent to give thionoesters in moderate to good yields. Notably, this methodology demonstrates a broad substrate scope, as alkyl/aryl alcohols are well tolerated, and this process might facilitate the synthesis of sulfur-containing compounds under simple and mild conditions. This journal is
Base-Catalyzed Transesterification of Thionoesters
Newton, Josiah J.,Britton, Robert,Friesen, Chadron M.
, p. 12784 - 12792 (2018/10/20)
Here we report a convenient synthesis of thionoesters by base-catalyzed transesterification. Benzyl and alkyl thionobenzoates and thionoheterobenzoates were efficiently prepared using various alcohols catalyzed by the corresponding sodium alkoxide. This methodology features a broad substrate scope, good to excellent yields, short reaction times, while simultaneously driving the reaction toward completion through the removal of the methanol byproduct. We also report the conversion of a small collection of thionobenzoates into the corresponding α,α-difluorobenzyl ethers to demonstrate the conversion of alcohols into difluorobenzyl or difluoroheterobenzyl ethers, a process that could prove useful for lead optimization in medicinal chemistry.
