Nickel-electrocatalysed C(sp3)–C(sp3) cross-coupling of unactivated alkyl halides

The C( sp 3 )–C( sp 3 ) linkages are undoubtedly important in natural products, pharmaceuticals and organic compounds. Electrochemical cross-electrophile coupling with a broad range of available alkyl halides is an attractive and useful strategy for the construction of C( sp 3 )–C( sp 3 ) bonds, although success could only be seen on activated alkyl halides in previous reports, due to the great challenge of reactivity and selectivity control of unactivated alkyl halides. Here we report a general strategy for electrochemical cross-electrophile coupling of unactivated alkyl halides under nickel catalysis. The highly selective electrochemical cross-electrophile coupling process was carried out in an operationally simple manner with high selectivity, setting the stage for the challenging C( sp 3 )–C( sp 3 ) bonds construction with versatile unactivated alkyl halides, including the cross-coupling of primary–primary halides, primary–secondary halides, primary–tertiary halides and secondary–secondary halides with high selectivity and excellent functional group compatibility. The diverse products, as well as the various late-stage modifications of bio-relevant compounds, demonstrated its potential use in organic synthesis and pharmaceutical chemistry. Electrochemical cross-electrophile coupling with alkyl halides for the construction of C( sp 3 )–C( sp 3 ) bonds is generally limited to activated alkyl halides. Now this approach is extended to coupling of unactivated alkyl halides using a nickel catalyst under mild conditions.