Suzuki–Miyaura coupling with high turnover number using an N-acyl- N-heterocyclic carbene palladacycle precursor

• Published in: Tetrahedron letters Vol. 45; no. 20; pp. 3849 - 3853
• Main Authors: Palencia, Hector, Garcia-Jimenez, Federico, Takacs, James M.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 10.05.2004; Elsevier
• Subjects: Biaryls; Catalysis; Chemistry; Chemistry, Organic; Coumarin synthesis; N-Acyl- N-heterocyclic carbene; N-Heterocyclic carbene ligand; NHC; Palladium catalyst; Physical Sciences; Science & Technology; Suzuki–Miyaura coupling; Suzuki–Miyaura coupling; N-Heterocyclic carbene ligand; Palladium catalyst; NHC; Catalysis; Biaryls; Coumarin synthesis; N-Acyl- N-heterocyclic carbene; coumarin synthesis; PALLADIUM; CATALYZED BISDIENE CARBOCYCLIZATIONS; COMPLEXES; palladium catalyst; catalysis; HECK REACTIONS; Suzuki-Miyaura coupling; ARYL BROMIDES; ALCOHOLS; N-acyl-N-heterocyclic carbene; biaryls; LIGANDS; C-C; CHLORIDES; HOMOGENEOUS CATALYSIS; N-heterocyclic carbene ligand
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2004.03.138

A simple N-acylimidazolium salt precursor to a NHC gives high turnover numbers (>1 7) in the Suzuki–Miyaura coupling. A simple N-acylimidazolium salt precursor to a NHC-complexed palladacyclic ligand gives high turnover numbers (>10 7) for Suzuki–Miyaura coupling and is applied to the preparation of biaryls used in the synthesis of coumarins. The results suggest that N-acyl-NHC derivatives can contribute to further expanding the rich chemistry of NHCs.