942-96-1Relevant 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
A Convenient Synthesis of Difluoroalkyl Ethers from Thionoesters Using Silver(I) Fluoride
Newton, Josiah,Driedger, Daniel,Nodwell, Matthew B.,Schaffer, Paul,Martin, Rainer E.,Britton, Robert,Friesen, Chadron M.
supporting information, p. 15993 - 15997 (2019/11/19)
Herein we report the mild and rapid fluorodesulfurization of thionoesters using only silver(I) fluoride. This reaction demonstrates excellent functional group tolerance and complements existing strategies for difluoroalkyl ether synthesis, which rely on t
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.
