title: N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C-H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes.
abstract: A novel class of N-doped cationic PAHs (polycyclic aromatic hydrocarbons) bearing the benzo[c,d]fluoranthene scaffold has been synthesized by the Rh(III)-catalyzed double-oxidative annulation of 2-arylbenzimidazoles with alkynes. The overall process involves a double C-N bond formation through a double C-H/N-H functionalization.The solid-state structures and electronic properties of the new N-doped PAHs were analyzed. These cationic azapolycycles were readily reduced in the presence of LiAlH4or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.
authors.affiliation: Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Dpto. de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
authors.forename: José M
authors.initials: JM
authors.lastname: Villar
authors.affiliation: Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Dpto. de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
authors.forename: Jaime
authors.initials: J
authors.lastname: Suárez
authors.affiliation: Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Dpto. de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
authors.forename: Jesús A
authors.identifier: 0000-0001-8499-4257
authors.initials: JA
authors.lastname: Varela
authors.affiliation: Centro Singular de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS) e Dpto. de Química Orgánica, Universidade de Santiago de Compostela , 15782 Santiago de Compostela, Spain.
authors.forename: Carlos
authors.identifier: 0000-0003-3213-4604
authors.initials: C
authors.lastname: Saá