Abstract:
Catalytic hydroarylation reactions of conjugated
dienes are achieved using tris(pentafluorophenyl)borane as a Lewis
acid catalyst under mild reaction conditions. This new protocol
shows a broad substrate scope for the highly regioselective
functionalization of sterically hindered aniline derivatives. Experimental and extensive density functional theory mechanistic studies
show that the complex of residual water and B(C6F5)3 plays a
crucial role in the aryl-assisted protonation of conjugated dienes,
forming allyl cation intermediates that induce the facile electrophilic aromatic substitution of aniline substrates.
