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We report herein an alkenylation of benzylic C(sp3)–H bonds with diazo compounds via carbon cation intermediates with DDQ as the oxidant in the presence of a catalytic amount of Fe(II). Diphenylmethane, toluene, benzyl methyl sulfide and their derivatives could be applied as substrates to afford the tetra-substituted olefin products, which may serve as useful building blocks in organic synthesis.

Graphical abstract: Fe(ii)-Catalyzed alkenylation of benzylic C–H bonds with diazo compounds

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