An Efficient Suzuki-Miyaura Coupling of Aryl Sulfamates and Boronic Acids Catalyzed by NiCl2(dppp)

• Published in: European journal of organic chemistry Vol. 2012; no. 19; pp. 3575 - 3579
• Main Authors: Chen, Guo-Jun, Han, Fu-She
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.07.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: B derivatives; Biaryls; Boronic acids; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Cross-coupling; Exact sciences and technology; General and physical chemistry; Nickel; Noncondensed benzenic compounds; Organic chemistry; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Science & Technology; Sulfur; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; HALIDES; ACTIVATION; Cross-coupling; ARENESULFONATES; MESYLATES; Nickel; Sulfur; Biaryls; ELECTROPHILES; Boronic acids; BIARYL CONSTRUCTION; Acid catalysis; Organic sulfide; Organic amidosulfate; Suzuki coupling; Biaryl derivative; Nickel II Chlorides; Cross reaction; Boron Organic compounds; Aromatic compound; Boronic acid derivative; Catalyst; Functional group
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200444

The Suzuki–Miyaura cross‐coupling of aryl sulfamates and boronic acids was investigated by using [1,3‐bis(diphenylphosphanyl)propane]nickel(II) chloride {NiCl2(dppp)} as the catalyst. The results showed that NiCl2(dppp) is a highly active and general catalyst that allows effective Suzuki–Miyaura cross‐coupling of aryl sulfamates with a slight excess amount of the boronic acid (1.2 equiv.) in the presence of a low catalyst loading (generally 1.0–1.5 mol‐%). The method also displays broad generality not only to various aryl sulfamates, but also to an array of boronic acids. Furthermore, various functional groups are tolerated. These apparent advantages make NiCl2(dppp) a practical and reliable catalyst system for the Suzuki–Miyaura coupling of aryl sulfamates. The NiCl2(dppp)‐catalyzed Suzuki–Miyaura cross‐coupling of aryl sulfamates and boronic acids was investigated. NiCl2(dppp) was found to be a highly active and general catalyst that can be used in small quantities (1.0–1.5 mol‐%). The method displays broad generality not only to various aryl sulfamates, but also to an array of boronic acids. Furthermore, various functional groups are tolerated.