Rh catalyzed olefination and vinylation of unactivated acetanilides

Abstract

In the catalyzed oxidative olefination of acetanilides (oxidative-Heck coupling), Rh offers great advantages over more common Pd catalysts. Lower catalyst loadings, large functional group tolerance (in particular to halides), and higher reactivity of electron-neutral olefins (styrenes) are some of the attractive features. Most interestingly, even ethylene reacts to yield the corresponding acetanilido-styrene. Moreover, the Cu(II) oxidant can also be utilized in catalytic amounts with air serving as the terminal oxidant.