Cross-Coupling Reactions between Alkenes by C–H Cyclometalation

Abstract

Alkenes are one of the most abundant raw feedstocks to construct complex chemicals, cross-coupling reactions using alkenes provides powerful methods toward valuable chemicals. In the past decade, cross-coupling reaction of simple alkenes by chelation-assisted alkenyl C−H functionalization has attracted many attentions due to its atom- and step efficiency, as well as excellent Z/E selectivity, proceeding by C−H exo-cyclometallation and endo-cyclometallation. In this Account, we would like to summarize transition-metal-catalyzed cross-coupling reactions between alkenes to generate 1,3-dienes by C−H alkenylation,1,4-dienes by C−H allylation, multi-substituted alkenes by hydroalkenylation, and heterocycles by tandem alkenyl C-H functionalization/annulation. Asymmetric alkenyl C−H alkenylation to prepare axially chiral aryl 1,3-dienes was also included.