16066-33-4Relevant articles and documents
Rare-Earth-Catalyzed Transsulfinamidation of Sulfinamides with Amines
Tu, Tao,Wang, Chaoyu,Wen, Daheng,Zheng, Qingshu
supporting information, p. 3718 - 3723 (2021/05/31)
A rare-earth-catalyzed transsulfinamidation of primary sulfinamides with alkyl, aryl, and heterocyclic amines for the synthesis of diverse secondary and tertiary sulfinamides has been realized. Unlike transition metal-catalyzed cross-coupling approaches restricted to non-commercially available disubstituted O-benzoyl hydroxylamines, this newly developed protocol is suitable for diverse readily available primary and secondary amines without any modifications. Excellent catalytic activity and selectivity are achieved with Eu(OTf)3 under mild reaction conditions, which extends the applicability of rare-earth catalysis.
Copper-Catalyzed Transsulfinamidation of Sulfinamides as a Key Step in the Preparation of Sulfonamides and Sulfonimidamides
Yu, Hao,Li, Zhen,Bolm, Carsten
supporting information, p. 15602 - 15605 (2018/11/10)
Secondary or tertiary sulfinamides are prepared by copper-catalyzed transsulfinamidation of primary sulfinamides with O-benzoyl hydroxylamines. Subsequent oxidations of the resulting products lead to the corresponding sulfonamides. Treatment of N-aryl sulfinamides with O-benzoyl hydroxylamines under copper catalysis provides N-aryl sulfonimidamides.
Efficient Synthesis of Sulfinate Esters and Sulfinamides via Activated Esters of p -Toluenesulfinic Acid
Gafur, Sayed Habibul,Waggoner, Stephanie L.,Jacobsen, Eric,Hamaker, Christopher G.,Hitchcock, Shawn R.
, p. 4855 - 4866 (2018/12/13)
Sulfinate esters were prepared by the process of activating p -toluenesulfinic acid with either cyanuric chloride, methanesulfonyl chloride, or 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCl). Activation of p -toluenesulfinic acid with cyanuric chloride led to the formation of sulfinate esters that were accompanied by the formation of the corresponding sulfones. The use of methanesulfonyl chloride for activation via methanesulfonic p -toluenesulfinic anhydride afforded mixtures of sulfinate esters and methanesulfonates. The use of the carbodiimide EDC proved to yield the best results with the highly selective formation of the target sulfinate esters. The use of trimethylacetic p -toluenesulfinic anhydride or cyanuric chloride to achieve the synthesis of sulfinamides proved to be ineffective due to poor chemoselectivity of the nucleophilic attack on the activated p -toluenesulfinic acid anhydride. Ultimately, the use of EDC-HCl to form the sulfinamides proved to be the best pathway for synthesis.
