An indole-amide-based phosphine ligand enabling a general palladium-catalyzed sterically hindered Suzuki–Miyaura cross-coupling reaction. Issue 7 (26th January 2022)

• Record Type: Journal Article
• Authors: Ng, Shan Shan; Chen, Zicong; Yuen, On Ying; So, Chau Ming
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 7(2022)
• Page Start: 1373
• Page End: 1378
• Publication Date: 2022-01-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob02294f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A novel family of indole-amide-based phosphine ligands was designed and synthesized. 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 κ 2 -P, O-coordination of L1 with palladium.