Organic Letters
Organic Letters
5 years ago

Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene

Synthesis, Optical Properties, and Regioselective Functionalization of 4a-Aza-10a-boraphenanthrene
Obis Castaño, Juan J. Vaquero, Adrián Pérez-Redondo, Luis Manuel Frutos, Patricia García-García, Alberto Abengózar, Diego Sampedro, David Sucunza
4a-Aza-10a-boraphenanthrene has been synthesized in only four steps from commercially available materials with a remarkable overall yield of 62%. In contrast to other BN-isosteres of phenathrene, this isomer is weakly fluorescent, which has been explained by means of computational studies that found a low energy conical intersection for the nonradiative deactivation of the excited state. Moreover, a completely regioselective functionalization of 4a-aza-10a-boraphenanthrene at C-1 by reaction with activated electrophiles has been achieved.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01435

DOI: 10.1021/acs.orglett.7b01435

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