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Nickel-catalysed Carbonylative Homologation Of Aryl Iodides

Jin-Bao Peng, Fu-Peng Wu, X. Qi, J. Ying, X. Wu
Published 2018 · Chemistry

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Homologation is an important organic transformation which extends the carbon chain of a parent molecule, and many procedures have been established. However, although carbonylation reactions are now well developed as valuable methods for the synthesis of carbonyl-containing compounds, studies of carbonylative homologation are limited. Here we report a nickel-catalysed carbonylative homologation of aryl iodides. With molybdenum hexacarbonyl as the solid carbon monoxide source and silane as the deoxygenation reagent, benzylic units can be effectively produced. Various (hetero)arenes can be successfully benzylated and give the corresponding products in moderate to excellent yields.Carbonylative homologation reactions are typically catalysed by precious metal catalysts such as palladium and rhodium. Here, aryl iodides are reductively homologated using a nickel triflate catalyst and simple bipyridine ligand, using Mo(CO)6 as the carbonyl source and phenyl silane as the reductant.
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