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Substrate-Paired Electron Donor-Acceptor Complexes Enable Photochemical Alkyl-Alkyl Cross-Coupling
Sodai Nishino1, Kento Inamura1, Takuya Kurahashi1
1Department of Chemistry, Graduate School of Science and Technology, Kwansei Gakuin University, Sanda, Hyogo669-1330, Japan.
None:
Selective C(sp3)-C(sp3) cross-coupling of two distinct alkyl radicals is difficult because homocoupling and radical decomposition compete with heterocoupling. We report a catalyst-free, redox-neutral photochemical coupling of alkylpyridinium salts with alkylboron reagents under mild conditions. Amino-acid-derived pyridinium salts and benzylic or nonbenzylic alkylboron partners participate with useful cross-selectivity. Mechanistic studies support photoexcitation of a substrate-paired EDA complex, followed by substrate-to-substrate electron transfer and radical-pair recombination.
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