An indole-amide-based phosphine ligand enabling a general palladium-catalyzed sterically hindered Suzuki-Miyaura
Shan Shan Ng1, Zicong Chen1, On Ying Yuen1
1State Key Laboratory of Chemical Biology and Drug Discovery and Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong. chau.ming.so@polyu.edu.hk.
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.
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