17075-02-4Relevant academic research and scientific papers
Synthesis of Functionalized Triphenylenes via a Traceless Directing Group Strategy
Yang, Shuai,Wang, Feng,Wu, Yanqi,Hua, Wenkai,Zhang, Fengzhi
, p. 1491 - 1495 (2018)
A novel ligand-free Pd-catalyzed cascade reaction between o-chlorobenzoic acids and cyclic diaryliodonium salts is reported. This one-pot procedure involves a carboxylic acid directed o-arylation followed by intramolecular decarboxylative annulation affording various valuable triphenylenes, which can be further transformed into diversified building blocks for material chemistry. For the first time, it was shown that an aromatic halide can react with diaryliodonium salts under the direction of carboxylic acid functionality. It was also demonstrated that the carboxylic acid could be employed as both a traceless directing group and functional handle for the atom- and step-economical one-pot double cross-coupling annulation reaction with cyclic diaryliodonium salts as the π-extending agents.
Studies on Intramolecular NH-Bridging in Aromatic Compounds.
Horaguchi, Takaaki,Klemm, L. H.,Norris, Eric S.
, p. 797 - 802 (2007/10/03)
A study was made of the use of calcium oxide as a catalyst at a temperature of 400 - 700 deg for the dehydrocyclization of four primary arylamines: 2-aminobiphenyl, 1-aminotriphenylene (5c), 2-phenoxyaniline, and N-(2-aminophenyl)pyrrole.Maximal yields of cyclized products isolated were 53percent (carbazole), 52percent (4H-naphthocarbazole), 18percent (phenoxazine), and 0percent, respectively.Comparison is made with reported cyclizations of the corresponding nitro and azido starting materials.In one case, treatment of 1-nitrotriphenylene with triethyl phosphite produced mainly diethyl N-(1-triphenylenyl)phosphoramidate (51percent).Mono- and hemihydrochlorides of 5c are described.A mechanism for the catalyzed dehydrocyclization is proposed.
