Mn(OAc)3‐Mediated Sulfonylation of Vinyl Azides Resulting in N‐Unsubstituted Enaminosulfones. Issue 38 (8th October 2021)

• Record Type: Journal Article
• Authors: Mulina, Olga M.; Doronin, Mikhail M.; O. Terent'ev, Alexander
• Is Part Of: ChemistrySelect. Volume 6:Issue 38(2021)
• Page Start: 10250
• Page End: 10252
• Publication Date: 2021-10-08
• Subjects: manganese (III) acetate -- oxidation -- sulfinates -- sulfonylation -- vinyl azides; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202102372
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: Mn(OAc)3 ‐mediated sulfonylation of vinyl azides with the use of sodium sulfinates was developed. As a result, N ‐enaminosulfones are formed in high yields. The reaction proceeds through the generation of sulfonyl radical, its addition to the double bond of vinyl azide resulting in elimination of N2 molecule and formation of iminyl radical, which is converted on the final step to the desired product. One of the main features of the developed process is application of substoichiometric amount of Mn(OAc)3 due to participation of the generated iminyl radical in the oxidation of the starting sulfinate. Abstract : Oxidative sulfonylation of vinyl azides under the action of Mn(OAc)3 was developed. Sodium sulfinates were used as precursors of sulfonyl radicals, which are added to the double bond of vinyl azides and result in the generation of iminyl radicals‐key intermediates. As a result, N ‐unsubstituted enaminosulfones were obtained in high yields.