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Singh V, Verma RS, Khatana AK, et al. Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization. J Org Chem. 2019;84(21):14161-14167doi: 10.1021/acs.joc.9b01644.
Singh, V., Verma, R. S., Khatana, A. K., & Tiwari, B. (2019). Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization. The Journal of organic chemistry, 84(21), 14161-14167. https://doi.org/10.1021/acs.joc.9b01644
Singh, Vikram, et al. "Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization." The Journal of organic chemistry vol. 84,21 (2019): 14161-14167. doi: https://doi.org/10.1021/acs.joc.9b01644
Singh V, Verma RS, Khatana AK, Tiwari B. Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization. J Org Chem. 2019 Nov 01;84(21):14161-14167. doi: 10.1021/acs.joc.9b01644. Epub 2019 Oct 14. PMID: 31552743.
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J Org Chem. 2019 Nov 01;84(21):14161-14167. doi: 10.1021/acs.joc.9b01644. Epub 2019 Oct 14.

Construction of Phenanthrenes and Chrysenes from β-Bromovinylarenes via Aryne Diels-Alder Reaction/Aromatization.

The Journal of organic chemistry

Vikram Singh, Ram Subhawan Verma, Anil K Khatana, Bhoopendra Tiwari

Affiliations

  1. Division of Molecular Synthesis & Drug Discovery , Centre of Biomedical Research, SGPGIMS-Campus , Raebareli Road , Lucknow 226014 , India.

PMID: 31552743 DOI: 10.1021/acs.joc.9b01644

Abstract

A highly efficient transition-metal-free general method for the synthesis of polycyclic aromatic hydrocarbons like phenanthrenes and chrysenes (and tetraphene) from β-bromovinylarenes and arynes has been developed. The reactions proceed via an aryne Diels-Alder (ADA) reaction, followed by a facile aromatization. This is the first report on direct construction of chrysenes (and tetraphene) using the ADA approach. Unlike the literature method which is limited to only 9/10-substituted derivatives, this method gives access to a wide variety of functionalized phenanthrenes.

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