N-Doped Cationic PAHs by Rh(III)-Catalyzed Double C–H Activation and Annulation of 2-Arylbenzimidazoles with Alkynes
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ISSN: 1523-7060
E-ISSN: 1523-7052
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American Chemical Society
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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 LiAlH4 or by the addition of PhLi to give interesting phenyl and diphenylmethanediamine derivatives.
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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
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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
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https://doi.org/10.1021/acs.orglett.7b00478Sponsors
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
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Copyright © 2017 American Chemical Society. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving