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Angew Chem Int Ed Engl. 2016 Jun 27;55(27):7728-32. doi: 10.1002/anie.201511424. Epub 2016 Apr 09.

Transition-Metal-Free Synthesis of Homo- and Hetero-1,2,4-Triaryl Benzenes by an Unexpected Base-Promoted Dearylative Pathway.

Angewandte Chemie (International ed. in English)

Mohammad Rehan, Sanjay Maity, Lalit Kumar Morya, Kaushik Pal, Prasanta Ghorai

Affiliations

  1. Department of Chemistry, Indian Institution of Science education and Research Bhopal, Bhopal By-pass Road, Bhouri, Bhopal, 462066, India.
  2. Department of Chemistry, Indian Institution of Science education and Research Bhopal, Bhopal By-pass Road, Bhouri, Bhopal, 462066, India. [email protected].

PMID: 27061117 DOI: 10.1002/anie.201511424

Abstract

An unprecedented approach for the synthesis of homo- and hetero-1,2,4-triaryl benzenes has been developed using a simple base-mediated reaction of either α-aryl cinnamyl alcohols or α,γ-di-aryl propanones. The salient feature of this strategy involves the sequential hydride transfer, regiospecific condensation, regiospecific dearylation, and aromatization under metal-free reaction conditions. The synthesis of unsymmetrically substituted triphenylenes by oxidative coupling of the synthesized 1,2,4-triaryl benzenes has also been demonstrated.

© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: arenes; cyclizations; materials science; regioselectivity; synthetic methods

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