Copper-catalyzed trifluoromethylation of aryl boronic acids using a CF3+ reagent

Abstract

A copper-catalyzed process for trifluoromethylation of aryl, heteroaryl, and vinyl boronic acids has been developed. The reaction is conducted under mild conditions and shows tolerance to moisture and a variety of functional groups.

Photocatalytic fluoroalkylation reactions of organic compounds

“…Trifluoromethylation has, in the past, relied on the use of transition metal catalysts, such as those containing Pd [22][23][24][25][26][27][28][29][30][31][32] and Cu [33][34][35][36][37][38][39][40][41][42][43][44][45][46] . Photoredox catalytic trifluoromethylation, fluoroalkylation and fluorination reactions provide a promising alternative to these existing methods, as it utilizes the environmentally benign protocols that rely on visible light or even sunlight irradiation.…”

An Improved Copper‐Mediated Oxidative Trifluoromethylation of Terminal Alkynes

“…We [8] and Buchwald [9] reported the Cumediated oxidative trifluoromethylation of boronic acids with the nucleophilic trifluoromethylation agent TMSCF 3 (Ruppert-Prakash reagent). Liu, [10] Sheng, [11] and Xiao [12] documented the Cu I -catalyzed trifluoromethylation of boronic acids with electrophilic trifluoromethylation agents (Umemoto reagent and Togni reagent). Noteworthy is that Hartwig [13] and Grushin [14] recently prepared the trifluoromethylation Cu reagent [(phen)CuCF 3 ] and [(phen)Cu-(PPh 3 )(CF 3 )], respectively, both of which reacted with aryl iodides to afford trifluoromethylated arenes in high yields.…”

Recent Advances of Trifluoromethylation

“…2011 年, 清华大学刘磊教授 [42] 和北京大学的王剑 波教授等 [43] 发现在铜催化下, 亲电三氟甲基化试剂与 未活化的烯烃反应可生成三氟甲基化的烯丙基化合物 (Scheme 13), 他们对反应机理也进行了探索. [26] , Hartwig [21] 和 Gooβen 等 [25] 进一步开展硼酸和硼酯的氧化三氟甲基 化反应; 刘磊 [38] 、沈其龙 [39] 和肖吉昌等 [40] 研究了芳基硼 酸与亲电三氟甲基化试剂的反应. …”