Electrochemical Imination of Sulfoxides Using N-Aminophthalimide

Abstract

[reaction: see text] A novel electrochemical sulfoxide imination process is described. Our approach starts with a highly selective nitrene transfer from N-aminophthalimide to a variety of sulfoxides. This oxidative treatment is followed by reductive N-N bond cleavage under the controlled current conditions, which leads to a range of parent NH sulfoximines. In addition to solving the challenging problem of removing the N-phthalimido group, the overall process avoids the use of toxic oxidants and metal additives.

Chemoselectivity and the Curious Reactivity Preferences of Functional Groups

“…By using this approach, a wide range of structurally dissimilar olefins have been transformed into the corresponding aziridines by Yudin and co-workers (Scheme 29). [54] The electrochemical aziridination process gives good to excellent yields for both electron-rich and electron-poor olefins. The range of olefins compares favorably with the metal-catalyzed aziridination processes, which usually have limited substrate scope.…”

Synthesis of chiral sulfoximines derived from 3-aminoquinazolinones and their catalysis of enantioselective diethylzinc addition to aldehydes

“…20,27,30- 36 Bolm and Okamura have studied the catalytic applications of a new class of sulfoximine ligands and their N-acylated derivatives. 41 In 1996, Bolm's group introduced sulfoximine as an enantiopure ligand in a Pd complex-catalyzed asymmetric allylation reaction, yielding the product with 73% ee. 41 In 1996, Bolm's group introduced sulfoximine as an enantiopure ligand in a Pd complex-catalyzed asymmetric allylation reaction, yielding the product with 73% ee.…”

Electrochemical strategies for C–H functionalization and C–N bond formation

“…[909][910][911] Likewise, under similar reaction conditions a variety of sulfoxides could be chemoselectively converted into the corresponding sulfoximines. 912 The Moeller group developed a protocol for synthesis of gand d-lactams using O-benzyl hydroxamates or N-phenyl amides. 913 Here, the anodically generated nitrogen-centered amidyl radicals 371 underwent cyclization reactions with electron-rich olefins to form carbon-centered radicals 372 that are subsequently oxidized to furnish carbocations 373.…”