Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction

Yoshio Nishimoto, Hiroki Kondo, Kazuya Yamaguchi, Daisuke Yokogawa, Junichiro Yamaguchi, Kenichiro Itami, Stephan Irle

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

The mechanism of an aromatic C-H coupling reaction between heteroarenes and arylboronic acids using a Pd catalyst was theoretically and experimentally investigated. We identified the C-B transmetalation as the rate-determining step. The (S)-catalyst-reactant complex was found to be stabilized by hyperconjugation between π-orbitals on the tolyl group and the S-O σ* antibonding orbital in the catalyst ligand. Our findings suggest routes for the design of new, improved Pd catalysts with higher stereoselectivity.

Original languageEnglish
Pages (from-to)4900-4906
Number of pages7
JournalJournal of Organic Chemistry
Volume82
Issue number9
DOIs
Publication statusPublished - 2017 May 5

ASJC Scopus subject areas

  • Organic Chemistry

Fingerprint Dive into the research topics of 'Theoretical Elucidation of Potential Enantioselectivity in a Pd-Catalyzed Aromatic C-H Coupling Reaction'. Together they form a unique fingerprint.

Cite this