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Synfacts 2021; 17(08): 0881
DOI: 10.1055/s-0040-1720362
Metals in Synthesis

Photochemical Asymmetric Iridium-Catalyzed C(sp3)–C(sp3) Cross-Coupling

Contributor(s):
Mark Lautens
,
Joachim Loup
Crisenza GE. M, Faraone A, Gandolfo E, Mazzarella D, Melchiorre P. * ICIQ, Institute of Chemical Research of Catalonia - the Barcelona Institute of Science and Technology, Tarragona and ICREA, Catalan Institution for Research and Advanced Studies, Barcelona, Spain
Catalytic Asymmetric C–C Cross-Couplings Enabled by Photoexcitation.

Nat. Chem. 2021;
13: 575-580
DOI: 10.1038/s41557-021-00683-5.
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Key words

iridium catalysis - asymmetric cross-coupling - photoredox catalysis - allylation

Significance

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.


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Comment

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.


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Publication History

Article published online:
20 July 2021

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