57751-98-1Relevant articles and documents
Electrophilic aromatic substitutions of aryltrifluoroborates with retention of the BF3- group: Quantification of the activating and directing effects of the trifluoroborate group
Berionni, Guillaume,Morozova, Varvara,Heininger, Maximilian,Mayer, Peter,Knochel, Paul,Mayr, Herbert
supporting information, p. 6317 - 6324 (2013/05/22)
Kinetics and mechanisms of transition-metal free reactions of furyl, thienyl and indolyl trifluoroborates with benzhydrylium (Ar2CH +) and iminium (Me2N+=CHR) ions have been investigated. In contrast to common belief, substitutions at CH positions are often faster than ipso-substitutions of the BF3K group, because BF3K activates the position attached to boron by a factor of 10 3-104 while adjacent CH positions are activated by factors of 105-106. Several reactions that have previously been interpreted as ipso-substitutions actually proceed via initial substitution at a vicinal or remote CH position, followed by protodeborylation. If the proton released during electrophilic substitution at a CH position is trapped by a base, the BF3- group can be preserved. Remote reactions of heteroaryl trifluoroborates with iminium ions provide straightforward access to novel zwitterionic ammonium or iminium trifluoroborates, which have been characterized by single-crystal X-ray analyses.
SbCl3-catalyzed one-pot synthesis of 4,4′-diamino- triarylmethanes under solvent-free conditions: Synthesis, characterization, and DFT studies
Bardajee, Ghasem Rezanejade
experimental part, p. 135 - 144 (2011/05/16)
A simple, efficient, and mild procedure for a solvent-free one-step synthesis of various 4,4′-diaminotriarylmethane derivatives in the presence of antimony trichloride as catalyst is described. Triarylmethane derivatives were prepared in good to excellent yields and characterized by elemental analysis, FTIR, 1H and 13C NMR spectroscopic techniques. The structural and vibrational analysis were investigated by performing theoretical calculations at the HF and DFT levels of theory by standard 6-31Gs *, 6-31G*/B3LYP, and B3LYP/cc-pVDZ methods and good agreement was obtained between experimental and theoretical results.
