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Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling
preprintsubmitted on 08.03.2021, 10:46 and posted on 10.03.2021, 12:54 by Tao Yang, Yi Wei, Ming Joo Koh
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.