Photoredox/Nickel Dual Catalysis Enables the Synthesis of Alkyl Cyclopropanes via C(sp3)-C(sp3) Cross Electrophile Coupling of Unactivated Alkyl Electrophiles

A facile synthesis of mono-, 1,1-and 1,2disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis is demonstrated. The challenging intramolecular C(sp(3))-C(sp(3)) cross-electrophile coupling of readily available unactivated 1,3-dialkyl electrophiles was performed under mild conditions that allowed traditionally reactive functional groups to be included. Mechanistic inspection and control experiments revealed the importance of dual catalysis and that the reaction proceeds via a stepwise oxidative addition followed by an intramolecular S(N)2 reaction.

Automated summary

A facile synthesis method for mono-, 1,1-and 1,2-disubstituted cyclopropanes via visible light-mediated photoredox/nickel dual catalysis under mild conditions was demonstrated. Mechanistic inspection and control experiments revealed the importance of dual catalysis and the reaction proceeds via a stepwise oxidative addition followed by an intramolecular S(N)2 reaction.