The Journal of organic chemistry

New Synthetic Approaches to Polycyclic Aromatic Hydrocarbons and Their Carcinogenic Oxidized Metabolites: Derivatives of Benzo [s] picene, Benzo [r st] …

FJ Zhang, C Cortez, RG Harvey

Index: Zhang, Fang-Jie; Cortez, Cecilia; Harvey, Ronald G. Journal of Organic Chemistry, 2000 , vol. 65, # 13 p. 3952 - 3960

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Citation Number: 55

Abstract

A new synthetic approach to polycyclic aromatic compounds is described that entails in the key steps double Suzuki coupling of PAH bisboronic acid derivatives with o-bromoaryl aldehydes to furnish aryl dialdehydes that are converted to larger polycyclic aromatic ring systems by either (a) conversion to diolefins by Wittig reaction followed by photocyclization or (b) reductive cyclization with triflic acid and 1, 3-propanediol. This synthetic method ...