Direct synthesis of ketones by the nickel-catalyzed reductive coupling between aryl, 1o, 2o, 3o-alkyl 2-pyridyl esters, and unactivated 1o, 2o-alkyl chlorides has been reported. This approach affords a highly efficient catalytic system to synthesize aryl-alkyl and dialkyl ketones produced in moderate to excellent yields with good functional group tolerance from easily accessible starting materials. Mechanistic studies reveal that the TBAI-mediated dynamic halide exchange process maintains a controlled low concentration of alkyl iodide, balancing the reactivity and cross-selectivity of alkyl chlorides.

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