Cationic Iridium-Catalyzed Asymmetric Decarbonylative Aryl Addition of Aromatic Aldehydes to Bicyclic Alkenes

Reina Nonami, Yusei Morimoto, Kazuya Kanemoto, Yasunori Yamamoto, Tomohiko Shirai

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

We report an unprecedented catalytic protocol for the enantioselective decarbonylative transformation of aryl aldehydes. In this process, the decarbonylation of aldehydes catalyzed by chiral iridium complexes enabled the formation of asymmetric C−C bonds through the formation of an aryl−iridium intermediate. The decarbonylative aryl addition to bicyclic alkenes was fluidly performed without a stoichiometric aryl−metal reagent, such as aryl boronic acid, with a cationic iridium complex generated in situ from Ir(cod)2(BArF4) and the sulfur-linked bis(phosphoramidite) ligand ((R,R)-S−Me−BIPAM). This reaction has broad functional group compatibility, and no waste is generated, except carbon monoxide.

Original languageEnglish
Article numbere202104347
JournalChemistry - A European Journal
Volume28
Issue number10
DOIs
Publication statusPublished - 2022 Feb 21
Externally publishedYes

Keywords

  • asymmetric catalysis
  • cationic iridium
  • C−H bond activation
  • decarbonylation
  • decarbonylative arylation

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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