3756-43-2Relevant articles and documents
Pyrrole-Based Anion-Responsive π-Electronic Molecules as Hydrogen-Bonding Catalysts
Hirata, Goki,Maeda, Hiromitsu
supporting information, p. 2853 - 2856 (2018/05/29)
The abilities of dipyrrolyldiketone boron complexes as hydrogen-bonding donor organocatalysts were examined by the Mannich-type reaction of N-acyl heteroarenium chlorides with 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene, as well as by the classical N-alkylation of amines with trityl chloride under base-free conditions. 1H NMR examinations of the hydrogen-bonding interaction between the pyrrole NH of the catalyst and the Cl- in the N-acyl heteroarenium salt suggested that the activation of N-acyl heteroarenium chlorides occurs through anion binding by the catalyst.
Transition-metal-free direct arylation of anilines
Pirali, Tracey,Zhang, Fengzhi,Miller, Anna H.,Head, Jenna L.,McAusland, Donald,Greaney, Michael F.
supporting information; scheme or table, p. 1006 - 1009 (2012/02/16)
Aryne arylation: A new method of direct arylation is reported for aniline substrates. The reaction uses benzyne to synthesize a variety of aminobiaryls under mild conditions (see scheme), requiring no stoichiometric metalation or transition-metal catalysis. An ene mechanism is implicated, and conveys excellent functional group tolerance relative to metal-mediated processes. Copyright
Preparations, X-ray crystal structure determinations, and base strength measurements of substituted tritylamines
Canle, Moises L.,Clegg, William,Demirtas, Ibrahim,Elsegood, Mark R.J.,Maskill, Howard
, p. 85 - 92 (2007/10/03)
A range of tritylamines TrNRR′, and 4-methoxy-, 4,4′-dimethoxy-, and 4,4′,4″-trimethoxy-substituted analogues, have been prepared from (substituted) trityl chloride, bromide, or tetrafluoroborate with ammonia or with amines HNRR′ where R and R′ are hydrog
The rearrangement of N-triarylmethyl anilines to their p-triarylmethyl derivatives
Siskos, Michael G.,Tzerpos, Nikolaos I.,Zarkadis, Antonios K.
, p. 759 - 768 (2007/10/03)
The N-triarylmethyl anilines Ph3C-NHAr (Ar = Ph, o-Me-C6H4, m-Me-C6H4, p-Me-C6H4, p-O2N-C6H4, p-Ph3C-C6H4) and Ar'3C-NHPh tBu-C6H4)3C> prepared by the reaction of Ph3C-Cl with anilines ArNH2 and of the corresponding chlorides Ar'3C-Cl with aniline (at 50-100 deg C), undergo a Hoffmann-Martius rearrangement to p-triarylmethyl derivatives (i.e., p-Ar'3C-C6H4-NH2 for Ar = Ph) when they are heated (ca. 185 deg C) with equimolar amounts of PhNH3(1+)Cl(1-).The latter catalyses the rearrangement probably through the formation of the instable anilinium salt Ar'3C-NH2Ar(1+)Cl(1-) that serves as a Ar'3C(1+) ion source.Ar'3C(1+) in a second step (electrophilic aromatic substitution) leads with excess of ArNH2 to p-substituted derivatives (e.g. p-Ar'3C-C6H4-NH2).A free radical mechanism, resonable in view of the high temperatures used (ca. 185 deg C), could be excluded; Ar'3C-NHAr undergoes homolysis of the C-N bond to Ar'3C. radicals at temperatures higher than 200 deg C, a fact which was established using ESR spectroscopy and product analysis.
