Synthesis of Functionalized Cyclopentene Derivatives through Gold-Catalyzed Reaction of Stabilized Vinyldiazo Compounds and Styrenes

Abstract

The reaction of alkenyldiazo compounds with styrene derivatives in the presence of [Au(IPr)(MeCN)][SbF6] provided cyclopentene derivatives resulting from a formal [3+2] cycloaddition reaction as major products. This reaction outcome stand in marked contrast with that previously observed for other olefinic derivatives. From a mechanistic point of view, this process would involve the initial generation of a highly electrophilic alkenylgold carbene intermediate, which would be subsequently involved in a stepwise carbocationic process.