A radical-radical cross-coupling reaction of xanthene with sulfonyl hydrazides: facile access to xanthen-9-sulfone derivatives.

Abstract

A straightforward strategy for direct incorporation of sulfonyl units into a xanthene moiety for accessing xanthen-9-sulfone derivatives in good to excellent yields has been established via metal-free radical-radical cross-coupling reaction of xanthenes and sulfonyl hydrazides. Using easily accessible starting materials, this methodology proceeds efficiently with a high degree of functional group compatibility and with a wide scope of both xanthenes and sulfonyl hydrazides under operationally simple reaction conditions. Mechanistic investigations revealed that sulfonyl radicals could be generated from sulfonyl hydrazides in the presence of TBHP under an oxygen atmosphere.