Straightforward and direct access to β-seleno- amines and sulfonylamides via the controlled addition of phenylselenomethyllithium (LiCH2SePh) to imines

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.