54773-20-5Relevant articles and documents
Solvated Nickel Complexes as Stoichiometric and Catalytic Perfluoroalkylation Agents**
Shreiber, Scott T.,Vicic, David A.
supporting information, p. 18162 - 18167 (2021/07/14)
The acetonitrile-solvated [(MeCN)Ni(C2F5)3]? was prepared in order to compare and contrast its reactivity with the known [(MeCN)Ni(CF3)3]? towards organic electrophiles. Both [(MeCN)Ni(CF3)3]? and [(MeCN)Ni(C2F5)3]? successfully react with aryl iodonium and diazonium salts as well as alkynyl iodonium salts to give fluoroalkylated organic products. Electrochemical analysis of [(MeCN)NiII(C2F5)3]? suggests that, upon electro-oxidation to [(MeCN)nNiIII(C2F5)3], reductive homolysis of a perfluoroethyl radical occurs, with the concomitant formation of [(MeCN)2NiII(C2F5)2]. Catalytic C?H trifluoromethylations of electron-rich arenes were successfully achieved using either [(MeCN)Ni(CF3)3]? or the related [Ni(CF3)4]2?. Stoichiometric reactions of the solvated nickel complexes reveal that “ligandless” nickel is exceptionally capable of serving as reservoir of CF3 groups under catalytically relevant conditions.
Trifluoromethylation of Arylsilanes with [(phen)CuCF3]
Morstein, Johannes,Hou, Haiyun,Cheng, Chen,Hartwig, John F.
, p. 8054 - 8057 (2016/09/13)
A method for the trifluoromethylation of arylsilanes is reported. The reaction proceeds with [(phen)CuCF3] as the CF3source under mild, oxidative conditions with high functional-group compatibility. This transformation complements prior trifluoromethylation of arenes in several ways. Most important, this method converts arylsilanes formed by the silylation of aryl C?H bonds to trifluoromethylarenes, thereby allowing the conversion of arenes to trifluoromethylarenes. The unique capabilities of the reported method are demonstrated by the conversion of a C?H bond into a C?CF3bond in active pharmaceutical ingredients which do not undergo this overall transformation by alternative functionalization processes, including a combination of borylation and trifluoromethylation.
Copper-mediated trifluoromethylation of arylboronic acids by trifluoromethyl sulfonium salts
Zhang, Cheng-Pan,Cai, Ji,Zhou, Chang-Bing,Wang, Xiao-Ping,Zheng, Xing,Gu, Yu-Cheng,Xiao, Ji-Chang
supporting information; experimental part, p. 9516 - 9518 (2011/10/02)
The ligand-free trifluoromethylation of arylboronic acids with a [Ph 2SCF3]+[OTf]-/Cu(0) system has been carefully investigated. Aryl-, alkenyl- and heteroarylboronic acids with a variety of functional groups were suitable substrates for this reaction. It is suggested that a CuCF3 species is formed under the reaction conditions.