Heterogeneous C–H alkenylations in continuous-flow: oxidative palladium-catalysis in a biomass-derived reaction medium

Abstract

Herein we report the unprecedented Fujiwara–Moritani reaction catalysed by the commercially available heterogeneous palladium catalyst Pd/C. The reaction works efficiently in GVL, a biomass derived solvent, in the coupling between variously substituted acetanilides and electron-poor alkenes, with complete selectivity towards the ortho-substitution. Moreover, the catalyst can be easily recycled and reused for consecutive reaction runs. We also developed a continuous-flow procedure, through an easily accessible tailor-made reactor, which allows the production of C–H alkenylated products on grams per hour scale.