Herein it is described that an indium(III) compound effectively catalyzes a reductive insertion into either diaryl or dialkyl disulfides with orthoesters to produce a variety of dithioacetal derivatives. This method could also be adapted to the diselenoacetalization of diselenides. During a series of reductive insertions using this method, it is noteworthy that an orthoester functions as a masked methylene moiety.
The reducing system (a black hammer) composed of an indium(III) catalyst and a hydrosilane could directly and reductively drive an orthoester (a conical wedge) that functions as a masked methylene moiety into the S−S bonds of diaryl or dialkyl disulfide derivatives, providing a variety of dithioacetal derivatives. It was demonstrated that this reducing system could also be effectively adapted to the diselenoacetalization of diaryl or dialkyl diselenides. More information can be found in the Full Paper by Norio Sakai et al.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.