Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes

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URI: http://hdl.handle.net/10347/15444
ISSN: 1523-7060
E-ISSN: 1523-7052
DOI: 10.1021/acs.orglett.7b00467

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2017-03-27

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American Chemical Society
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Abstract

2-Alkenyltriflylanilides react with allenes upon treatment with catalytic amounts of Pd(OAc)2 and Cu(II) to give highly valuable 2,3-dihydro-1H-benzo[b]azepines, in good yields, and with very high regio- and diastereoselectivities. Density functional theory (DFT) calculations suggest that the C–H activation of the alkenylanilide involves a classical concerted metalation–deprotonation (CMD) mechanism

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This is the peer reviewed version of the following article: Borja Cendón, Noelia Casanova, Cezar Comanescu, Rebeca García-Fandiño, Andrés Seoane, Moisés Gulías* and José L. Mascareñas*, Palladium-Catalyzed Formal (5+2) annulation between ortho-Alkenylanilides and Allenes. Org. Lett. 2017, 19, 1674-1677 [DOI: ]. This article may be used for non commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving

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Palladium-catalyzed| Ortho- alkenylanilides| Allenes

Bibliographic citation

Cendón, B., Casanova, N., Comanescu, C., Garcí­a-Fandiño, R., Seoane, A., Gulías, M. & Mascareñas, J.L. 2017, "Palladium-Catalyzed Formal (5 + 2) Annulation between ortho-Alkenylanilides and Allenes", Organic letters, vol. 19, no. 7, pp. 1674-1677

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This work has received financial support from Spanish grants (SAF2013-41943-R, SAF2016-76689-R, CTQ2015-74621-JIN and CTQ2016-77047-P), the Consellería de Cultura, Educación e Ordenación Universitaria (GRC2013-041, 2015-CP082 and Centro Singular de Investigación de Galicia accreditation 2016-2019, ED431G/09), the European Regional Development Fund (ERDF), and the European Research Council (Advanced Grant No. 340055). R. G.-F. thanks a FCT scholarship from Portugal. The orfeo-cinqa network CTQ2014-51912-REDC is kindly acknowledged. All calculations were carried out at Centro de Supercomputación de Galicia (CESGA)

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© 2017 American Chemical Society

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