401-79-6Relevant articles and documents
Benzylic Bromination by Bromotrichloromethane. Dependence of the Identity of the Chain-Carrying Radical(s) on the Method of Initiation
Krosley, Kevin W.,Gleicher, Gerald Jay
, p. 4469 - 4472 (1990)
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Cleavage of C(sp3)-F Bonds in Trifluoromethylarenes Using a Bis(NHC)nickel(0) Complex
Imiya, Hiroto,Iwamoto, Hiroaki,Ogoshi, Sensuke,Ohashi, Masato
, p. 19360 - 19367 (2020/11/13)
The first example of the oxidative addition of a C(sp3)-F bond in trifluoromethylarenes to a nickel(0) complex is described. A nickel(0) complex that bears two N-heterocyclic carbene (NHC) ligands of low steric demand is able to cleave C(sp3)-F bonds of trifluoromethylarenes to afford the corresponding trans-difluorobenzyl nickel(II) fluoride complexes. Isolation and characterization studies suggested that the cleavage of the C(sp3)-F bond proceeds via an η2-arene nickel(0) complex. Taking advantage of the reactivity of these nickel(II) fluoride complexes, we developed a catalytic hydrodefluorination of trifluoromethylarenes using hydrosilanes. A computational study indicated that the electron-rich nickel(0) center supported by two relatively small NHC ligands cleaves the C(sp3)-F bond via a syn-SN2′ mechanism.
Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent
Miyagawa, Masamichi,Ishikawa, Taisuke,Shinkai, Kota,Akiyama, Takahiko
supporting information, p. 29 - 31 (2019/01/04)
N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.