Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C–H Functionalization of o-Vinylphenols

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URI: http://hdl.handle.net/10347/18478
ISSN: 0002-7863
E-ISSN: 1520-5126
DOI: 10.1021/ja410538w

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2014

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American Chemical Society
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Readily available o-vinylphenols undergo a formal (5 + 2) cycloaddition to alkynes when treated with catalytic amounts of [Cp*RhCl2]2 and Cu(OAc)2. The reaction, which involves the cleavage of the terminal C–H bond of the alkenyl moiety, generates highly valuable benzoxepine skeletons in a practical, versatile, and atom-economical manner. Using carbon monoxide instead of an alkyne as reaction partner leads to coumarin products which formally result from a (5 + 1) cycloaddition

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This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Chemical Biology, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see: https://pubs.acs.org/doi/10.1021/ja410538w

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Seoane, A., Casanova, N., Quiñones, N., Mascareñas, J., & Gulías, M. (2014). Straightforward Assembly of Benzoxepines by Means of a Rhodium(III)-Catalyzed C–H Functionalization of o-Vinylphenols. J. Am. Chem. Soc., 136, 3, 834-837. DOI: 10.1021/ja410538w

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We are thankful for the financial support provided by the Spanish Grants (SAF2010-20822-C02 and CSD2007-00006 Consolider Ingenio 2010), the ERDF and the Xunta de Galicia Grants GRC2010/12, GR2013-041, INCITE09 209084PR and EM2013/036. M.G thanks Xunta de Galicia for a Parga Pondal contract

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© 2014 American Chemical Society

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