NIS-promoted intermolecular bis-sulfenylation of allenamides via a two-step radical process: synthesis of 1,3-dithioethers

Abstract

An efficient NIS-promoted two-step radical addition of thiols to allenamides was developed to create a workable route to 1,3-dithioethers. The reaction exhibited good functional group tolerance and high efficiency, affording the products in good to excellent yields. Moreover, cyclic dithioethers could be obtained by using 1,2-dithiols as substrates. Mechanistic investigations including calculation study indicated that a two-step radical process is likely involved in this transformation.