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Photochemical Asymmetric Iridium-Catalyzed C(sp3)–C(sp3) Cross-Coupling
Catalytic Asymmetric C–C Cross-Couplings Enabled by Photoexcitation.
Nat. Chem. 2021;
The Melchiorre group reports an enantioselective C(sp3)–C(sp3) cross-coupling of α-vinylbenzyl alcohols with radical precursors under visible-light irradiation. In contrast to the well-established ionic reactivity of allyl-iridium(III) catalysts, photoexcitation allowed for the activation of a coupling partner via a single-electron transfer manifold.
No external photocatalyst was required as the reaction relies on the photoexcitation of the chiral organometallic intermediate. In addition to Hantzsch ester derivatives, α-amino trimethylsilanes and tetrafluoroborates could be employed as radical precursors, typically with lower efficacy.
Article published online:
20 July 2021
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