RT Journal Article
T1 N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C–H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
A1 Villar Carabel, José Manuel
A1 Suárez Rivero, Jaime
A1 Varela Carrete, Jesús Ángel
A1 Saá Rodríguez, Carlos
K1 Alkynes
K1 2-Arylbenzimidazoles
K1 C-H activation
K1 Polycyclic aromatic hydrocarbons
K1 Rhodium
AB 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 LiAlH4 or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.
PB American Chemical Society
SN 1523-7060
YR 2017
FD 2017
LK http://hdl.handle.net/10347/23352
UL http://hdl.handle.net/10347/23352
LA eng
NO Villar, J. M., Suárez, J., Varela, J. A., Saá, C., (2017). N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C–H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes. Org. Lett. 19, 7, 1702-1705
NO NOTICE: This is the peer reviewed version of the following article: Villar, J. M., Suárez, J., Varela, J. A., Saá, C., (2017). N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C–H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes. Org. Lett. 19, 7, 1702-1705. [doi: 10.1021/acs.orglett.7b00478]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving
NO This work has received financial support from Spanish MINECO (project CTQ2014-59015R), the Consellería de Cultura, Educación e Ordenación Universitaria (project GRC2014/032) and Centro singu-lar de investigación de Galicia, accreditation 2016-2019, ED431G/09 and ERDF. We also thank the ORFEO-CINQA network (CTQ2014-51912REDC). J.M. V. and J. S. thank the Xunta de Galicia for pre-doctoral and postdoctoral contracts, respectively
DS Minerva
RD 23 abr 2026