4.8 Article

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

Journal

ACS CATALYSIS
Volume 12, Issue 12, Pages 6851-6856

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c01713

Keywords

gold catalysis; gold-carbenes; carbene transfer; Profen skeletons; DFT studies

Funding

  1. Ministerio de Ciencia e Innovacion - FEDER Una manera de hacer Europa [PID2020-113797RB-C21]
  2. Junta de Andalucia [P18-RT-1536]
  3. Universidad de Huelva [UHU-1260216]
  4. Research Council of Norway [314321]
  5. Centre of Excellence schemes [262695]
  6. Norwegian Metacenter for Computational Science (NOTUR) [nn4654k]

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The complete regioselective incorporation of carbene units to nonactivated arene rings has been achieved using gold(I) catalysts and readily available, nonelaborated ethyl 2-phenyldiazoacetate as the carbene source, which is in contrast with previous examples that required highly modified diazo compounds.
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 revealed the important role of the R group in the C(R)CO2Et fragment, which dramatically affects the energy profile of this transformation.

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