The reductive deoxygenation of anisole derivatives plays a key role in organic synthesis. For example, the reductive cleavage of C(aryl)-O bonds enables the use of a methoxy group as a removable activating and directing group in the functionalization of arenes. Although several nickel-catalyzed reactions for deoxygenation of a methoxy group using a hydrosilane reagent or hydrogen as a reductant have already been reported, all such reactions can only be applicable to π-extended ethers such as naphthyl and biphenyl ethers, and C(aryl)-O bonds of simple anisole derivatives cannot be reduced.<br/>Here, we report nickel-catalyzed reductive cleavage reaction of C(aryl)-O bonds of anisoles using an aminoborane reagent as a reductant. Unlike previously reported reactions, this method allows the effective reduction of C(aryl)-O bonds of simple anisole derivatives.

Nickel-catalyzed reductive cleavage of carbon-oxygen bonds in anisole derivatives using an aminoborane reagent

256th National Meeting (2018)

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