Straightforward Synthesis of Novel Acene-Based Aryne Precursors

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URI: http://hdl.handle.net/10347/16988
ISSN: 0936-5214
E-ISSN: 1437-2096
DOI: 10.1055/s-0034-1381005

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2015-06-11

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Thieme Publishing
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Abstract

Large polycyclic o-(trimethylsilyl)aryl triflates are easily obtained by reaction of commercially available bisaryne precursors with cyclopentadienones. The transformation involves controlled generation of one of the aryne functionalities, trapping by Diels–Alder reaction with a dienone, and chelotropic extrusion of CO. The newly synthesized triflates are precursors of acene-based arynes, including a didehydropentacene

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Arynes| Polycyclic aromatic hydrocarbons| Acenes| Diels–Alder reaction| Cycloadditions

Bibliographic citation

Peña, D., Pérez, D., Rodríguez-Lojo, D., & Guitián, E. (2015). Straightforward Synthesis of Novel Acene-Based Aryne Precursors. Synlett, 26(11), 1633-1637. doi: 10.1055/s-0034-1381005

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Financial support from the Spanish Ministry of Science and Competitiveness (MINECO, CTQ2013-44142-P and MAT2013-46593-C6-6-P), the European Union (Project PAMS, contract no. 610446), Xunta de Galicia (GPC2014/25), and FEDER is gratefully acknowledged. D.R.-L. thanks the Spanish Ministry of Education for the award of an FPU fellowship

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© Georg Thieme Verlag Stuttgart · New York

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica