A Mild and Efficient Method for Preparing Alkyl Phenyl Selenides from Alkyl Diphenyl Phosphinites

摘要

Alkyl phenyl selenides have recently attracted considerable interest since they can be used as precursors for various organic transformations. Additionally, selenides have played an important role in biochemical processes serving as therapeutic compounds ranging from antiviral and anticancer agents to naturally occurring food supplements. Although numerous methods for preparing alkyl phenyl selenides have been reported, these methods sometimes suffer from difficulties in handling the selenide reagent used as the selenium source, strongly basic or acidic reaction conditions, and low yields of tertiary alkyl phenyl selenides. Recently, we reported a mild procedure for the preparation of alkyl phenyl selenides from alkyl halides using PhSeSePh in the presence of In. This protocol has a number of advantages including a simple experimental procedure, neutral pH and mild reaction conditions, and high yields of the desired products even in the case of tertiary alkyl phenyl selenides. In an attempt to extend the scope of our methodology, we decided to explore the preparation of alkyl phenyl selenides under our conditions using a new type of precursor, alkyl diphenyl phosphinites (Scheme 1).