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Exhaustive Reduction of Esters Enabled by Nickel Catalysis

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journal contribution
posted on 28.04.2020, 16:37 by Adam Cook, Sekar Prakash, Yan-Long Zheng, Stephen G. Newman
We report a one-step procedure to directly reduce unactivated aryl esters into their corresponding tolyl derivatives. This is achieved by an organosilane-mediated ester hydrosilylation reaction and subsequent Ni/NHC-catalyzed hydrogenolysis. The resulting conditions provide a direct and efficient alternative to multi-step procedures for this transformation that often require the use of hazardous metal hydrides. Applications in the synthesis of −CD3-containing products, derivatization of bioactive molecules, and chemoselective reduction in the presence of other C–O bonds are demonstrated.