Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling for C(sp2)-C(sp3) and C(sp3)-C(sp3) Bond Formation

The construction of C-C bonds through cross-coupling between two electrophiles in the absence of excess metallic reducing agents is a desirable objective in chemistry. Here, we show that N-alkylpyridinium salts can be efficiently merged with aryl or alkyl halides in an intermolecular fashion, affording products in up to 92% yield at ambient temperature. These reactions harness the ability of N-alkylpyridinium salts to form electron donor-acceptor complexes with Hantzsch esters, enabling photoinduced singleelectron transfer and fragmentation to afford alkyl radicals that are subsequently trapped by a Ni-based catalytic species to promote C(sp(2))-C(sp(3)) and C(sp(3))-C(sp(3)) bond formation. The operationally simple protocol is applicable to site-selective cross-coupling and tolerates diverse functional groups, including those that are sensitive toward metal reductants.

Automated summary

This new method allows for efficient synthesis of C-C bonds at ambient temperature, with site-selective cross-coupling capability and tolerance toward various functional groups sensitive to metal reductants.