An indole-amide-based phosphine ligand enabling a general palladium-catalyzed sterically hindered Suzuki-Miyaura cross-coupling reaction

Shan Shan Ng, Zicong Chen, On Ying Yuen, Chau Ming So

Research output: Journal article publicationJournal articleAcademic researchpeer-review

Abstract

A novel family of indole-amide-based phosphine ligands was designed and synthesized. The Pd/InAm-phos (L1) catalytic system exhibited excellent efficiency in the Suzuki-Miyaura cross-coupling of sterically hindered (hetero)aryl chlorides to synthesize tri-ortho-substituted biaryls. Excellent product yields were obtained in a short reaction time (e.g., 10 min), and a Pd catalyst loading down to 50 ppm was also achieved. The oxidative addition adduct of Pd-L1 with 2-chlorotoluene was also well-characterized by single-crystal X-ray crystallography and showed a κ2-P,O-coordination of L1 with palladium.

Original languageEnglish
Pages (from-to)1373-1378
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume20
Issue number7
DOIs
Publication statusPublished - 21 Feb 2022

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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