Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling

10 March 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


The construction of carbon-carbon 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 90%
yield at ambient temperature. These reactions harness the ability of N-alkylpyridinium salts to form electron donor-acceptor complexes with Hantzsch esters, enabling photoinduced single-electron transfer and fragmentation to afford alkyl radicals that are subsequently trapped by a Ni-based catalytic species to promote C(sp2)-C(sp3) and
C(sp3)-C(sp3) bond formation. The operationally simple protocol is applicable to site-selective cross-coupling and tolerates diverse functional groups, including those that are sensitive towards metal reductants.


electron donor–acceptor complex
pyridinium salt


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