Room-temperature base-free copper-catalyzed trifluoromethylation of organotrifluoroborates to trifluoromethylarenes

• Published in: Tetrahedron Vol. 68; no. 48; pp. 9949 - 9953
• Main Authors: Huang, Yuanyuan, Fang, Xin, Lin, Xiaoxi, Li, Huaifeng, He, Weiming, Huang, Kuo-Wei, Yuan, Yaofeng, Weng, Zhiqiang
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 02.12.2012; Elsevier
• Subjects: B derivatives; Catalysis; Catalysts: preparations and properties; chemical reactions; chemical structure; Chemistry; Chemistry, Organic; Copper catalyst; Electrophilic trifluoromethylation reaction; Exact sciences and technology; Functional groups; General and physical chemistry; Noncondensed benzenic compounds; Organic chemistry; organic compounds; Organometalloidal and organometallic compounds; Physical Sciences; Preparations and properties; Science & Technology; temperature; Tetrahedrons; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; Trifluoromethylarenes; Electrophilic trifluoromethylation reaction; Trifluoromethylarenes; Copper catalyst; PALLADIUM; DI; ARENES; TERMINAL ALKYNES; FLUORINATION; OXIDATIVE TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; PERFLUOROALKYLATION; BORONIC ACIDS; ARYL IODIDES; Catalytic reaction; Chemical reagent; Transition metal; Electrophilic reaction; Organic borate; Copper ion; Trifluoromethylation; Benzenic compound; Boron Organic compounds; Aromatic compound; Copper; Catalyst; Room temperature; Electrophile; Functional group
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2012.09.083

An efficient room temperature copper-catalyzed trifluoromethylation of organotrifluoroborates under the base free condition using an electrophilic trifluoromethylating reagent is demonstrated. The corresponding trifluoromethylarenes were obtained in good to excellent yields and the reaction tolerates a wide range of functional groups. [Display omitted]