Ligand-enabled Ni-catalysed enantioconvergent intermolecular Alkyl-Alkyl cross-coupling between distinct Alkyl halides

Wen-Tao Zhao, Jian-Xin Zhang, Bi-Hong Chen and Wei Shu ()
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Wen-Tao Zhao: Southern University of Science and Technology
Jian-Xin Zhang: Southern University of Science and Technology
Bi-Hong Chen: Southern University of Science and Technology
Wei Shu: Southern University of Science and Technology

Nature Communications, 2023, vol. 14, issue 1, 1-7

Abstract: Abstract α-Tertiary aliphatic amides are key elements in organic molecules, which are abundantly present in natural products, pharmaceuticals, agrochemicals, and functional organic materials. Enantioconvergent alkyl-alkyl bond-forming process is one of the most straightforward and efficient, yet highly challenging ways to build such stereogenic carbon centers. Herein, we report an enantioselective alkyl-alkyl cross-coupling between two different alkyl electrophiles to access α-tertiary aliphatic amides. With a newly-developed chiral tridentate ligand, two distinct alkyl halides were successfully cross-coupled together to forge an alkyl-alkyl bond enantioselectively under reductive conditions. Mechanistic investigations reveal that one alkyl halides exclusively undergo oxidative addition with nickel versus in-situ formation of alkyl zinc reagents from the other alkyl halides, rendering formal reductive alkyl-alkyl cross-coupling from easily available alkyl electrophiles without preformation of organometallic reagents.

Date: 2023
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DOI: 10.1038/s41467-023-38702-3

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