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*

*この研究の対応する著者

研究成果: Article査読

11 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)4900-4906
ページ数7
ジャーナルJournal of Organic Chemistry
82
9
DOI
出版ステータスPublished - 2017 5 5

ASJC Scopus subject areas

  • 有機化学

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