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
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.
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.
