Nickel-Catalyzed Cross-Coupling of Aryl Phosphates with Arylboronic Acids

• Published in: Journal of organic chemistry Vol. 76; no. 7; pp. 2338 - 2344
• Main Authors: Chen, Hu, Huang, Zhongbin, Hu, Xiaoming, Tang, Guo, Xu, Pengxiang, Zhao, Yufen, Cheng, Chien-Hong
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.04.2011; Amer Chemical Soc
• Subjects: Boronic Acids - chemistry; Catalysis; Catalysts: preparations and properties; Chemical reactivity; Chemistry; Chemistry, Organic; Cross-Linking Reagents - chemistry; Exact sciences and technology; General and physical chemistry; Molecular Structure; Nickel - chemistry; Noncondensed benzenic compounds; Organic chemistry; Palladium - chemistry; Phosphates - chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; BORONIC ACIDS; ALKENYL PHOSPHATES; ORGANOBORON COMPOUNDS; C-O ACTIVATION; ENOL ETHERS; TEMPERATURE SUZUKI-MIYAURA; ESTERS; CARBON-CARBON BONDS; ALKYNES; GRIGNARD-REAGENTS; Catalytic reaction; Haloarene; Transition metal; Palladium; Selectivity; Phosphorus Organic compounds; Organic molecule; Suzuki-Miyaura cross-coupling; Cross reaction; Organic phosphate; Boron Organic compounds; Nickel complex; Aromatic compound; Nickel; Chemical reactivity; Chemical synthesis; Platinoid; Boronic acids; Catalyst; Halogen Organic compounds
• ISSN: 0022-3263; 1520-6904; 1520-6904
• DOI: 10.1021/jo2000034

The Suzuki−Miyaura cross-coupling of aryl phosphates using Ni(PCy3)2Cl2 as an inexpensive, bench-stable catalyst is described. Broad substrate scope and high efficiency are demonstrated by the syntheses of more than 40 biaryls and by constructing complex organic molecules. The poor reactivity of aryl phosphates relative to aryl halides is successfully employed to construct polyarenes by selective cross-coupling using Pd and Ni catalysts.