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Selective Functionalization of Arene C(sp²)-H Bonds by Gold Catalysis: The Role of Carbene Substituents.

ABSTRACT: The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved employing gold(I) catalysts bearing alkoxydiaminophosphine ligands, with readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source. These results are in contrast with the scarce precedents which required highly elaborated diazo substrates. Density functional theory (DFT) calculations have revealed the important role of the R group in the C(R)CO₂Et fragment, which dramatically affects the energy profile of this transformation.

SUBMITTER: Pizarro JD

PROVIDER: S-EPMC9210454 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Selective Functionalization of Arene C(sp2)-H Bonds by Gold Catalysis: The Role of Carbene Substituents.

Pizarro Juan Diego JD Schmidtke Inga L IL Nova Ainara A Fructos Manuel R MR Pérez Pedro J PJ

ACS catalysis 20220525 12

The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved employing gold(I) catalysts bearing alkoxydiaminophosphine ligands, with readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source. These results are in contrast with the scarce precedents which required highly elaborated diazo substrates. Density functional theory (DFT) calculations have revealed the important role of the R group in the C(R)CO2Et fragment, ...[more]

PMID: 35756859

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