Nature - Electrochemically driven cross-electrophile coupling of alkyl halides
. Owing to the broad availability of alkyl halides, their direct cross coupling—commonly known as cross-electrophile-coupling —provides a promising route toward this objective. Such transformations circumvent the preparation of carbon nucleophiles used in traditional cross-coupling reactions as well as stability and functional group tolerance issues that commonly associate with these reagents. However, achieving high selectivity in C-C XEC remains a largely unmet challenge.
Here, we employ electrochemistry to achieve the differential activation of alkyl halides by exploiting their disparate electronic and steric properties. Specifically, the selective cathodic reduction of a more substituted alkyl halide gives rise to a carbanion, which undergoes preferential coupling with a less substituted alkyl halide via bimolecular nucleophilic substitution to forge a new C–C bond.
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