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Koh_Chemrxiv_2021_combined.pdf (10.93 MB)

Photoinduced Nickel-Catalyzed Deaminative Cross-Electrophile Coupling

preprint
submitted 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.

Funding

National University of Singapore Academic Research Fund Tier 1: R-143-000-B57-114

History

Email Address of Submitting Author

chmkmj@nus.edu.sg

Institution

National University of Singapore

Country

Singapore

ORCID For Submitting Author

0000-0002-2534-4921

Declaration of Conflict of Interest

No conflict of interest.

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ChemRxiv

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