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A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position

Alberto Abengózar, David Sucunza, Patricia García-García, Diego Sampedro, Adrián Pérez-Redondo, Juan J Vaquero

J Org Chem. 2019 Jun 7;84(11):7113-7122.

PMID: 31079459

Abstract:

3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all nonsubstituted BN-phenanthrenes reported to date (ϕF = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds toward organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP827543 2-Vinylnaphthalene 2-Vinylnaphthalene 827-54-3 Price
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