Straightforward and direct access to β-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines. Issue 51 (18th December 2020)

• Record Type: Journal Article
• Authors: Senatore, Raffaele; Malik, Monika; Touqeer, Saad; Listro, Roberta; Collina, Simona; Holzer, Wolfgang; Pace, Vittorio
• Is Part Of: Tetrahedron. Volume 76:Issue 51(2020)
• Publication Date: 2020-12-18
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2020.131220
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: The transfer of a α-methyl phenylseleno carbanion to variously functionalized N -aryl and N- sulfonyl imines is reported. The fast selenium-lithium exchange conducted on a diselenoacetal with n -BuLi enables the generation of the attacking homologative nucleophile under chemoselective conditions preserving concomitant potentially sensitive functionalities to the lithiating conditions. Uniformly high yields were observed, thus establishing a valuable and conceptually simple approach to the title compounds. Graphical abstract: Image 1