14934-00-0Relevant articles and documents
Synthetic preparation of N-alkyl and N-aryl arenesulfinamides using an arenesulfinic acid-CDI driven approach
Austermuehle, Brad J.,Collins, Erin S.,Hamaker, Christopher G.,Hitchcock, Shawn R.
supporting information, p. 3483 - 3491 (2021/10/14)
A new synthetic methodology has been developed for the synthesis of N-alkyl and N-aryl arenesulfinamides. The methodology involved reacting arenesulfinic acids (R = -Me, -H, -Cl) with 1,1’-carbonyldiimidazole (CDI) to form the reactive intermediate, an arenesulfinylimidazole. This intermediate was then reacted with both primary and secondary amines to yield the corresponding N-alkyl sulfinamides in yields up to 90%. While the overall yields ranged from 52% to 90%, the level of diastereoselection with racemic or enantiomerically enriched amines only reached a level of 54:46 favoring the major diastereomer as determined by analysis of the 500 MHz 1H NMR spectra. A series of aniline derivatives were also investigated as coupling partners and were found to form the N-aryl arenesulfinamide in good yield.
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.
Palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides
Sun, Xiaofei,Tu, Xingzhao,Dai, Chuan,Zhang, Xiaoping,Zhang, Binbin,Zeng, Qingle
supporting information; experimental part, p. 4454 - 4459 (2012/07/03)
The palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides is reported. In the presence of Pd2(dba)3, tBuXPhos, NaOH, and a small amount of water, the C-N cross coupling of chiral tert-butanesulfinamide and aryl halides was accomplished to give N-aryl tert-butanesulfinamide without racemization, and the coupling of racemic p-toluenesulfinamide smoothly afforded N-aryl p-toluenesulfinamides. 2-Bromopyridine was also suitable for the coupling. Addition of a small amount of water to the catalytic system was of importance to obtain high yields.