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Alkyl–alkyl C–C bond formation with olefin

Carbon–carbon bond formation, including between sp3-hybridized carbon centres (that is, alkyl groups), is most often carried out by cross-coupling of an electrophile and an organometallic reagent. Here, Greg Fu and colleagues report a new strategy for alkyl–alkyl carbon–carbon bond formation, the most challenging combination, using an olefin in place of the organometallic reagent. The nickel-catalysed asymmetric reductive coupling between alkyl halides and olefins in the presence of a hydrosilane resulted in the formation of products in high yield and enantioselectivity. This enantioconvergent process works for tertiary alkyl halides, converting a racemic starting material into an enantioenriched product with a quaternary stereocentre. The reaction provides access to various chiral building blocks from simple starting materials, including alkynes and perfluoroalkyl-containing electrophiles.

Nature 563, 7731 table of contents

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