Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes

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2021_acs.orglett.bello_nonplanar.pdf (1.4 MB)
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URI: http://hdl.handle.net/10347/26643
ISSN: 1523-7060
E-ISSN: 1523-7052
DOI: 10.1021/acs.orglett.1c01881

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2021

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American Chemical Society
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Abstract

A novel tandem Ru-catalyzed [2 + 2 +2] cycloaddition of arylenynes to dihydrobiphenylenes followed by halogen-radical ring opening has been developed for the construction of tub-shaped halogenated benzocyclooctatetraenes (bCOTs). Cross-couplings and Diels-Alder reactions of the brominated bCOTs allow the formation of the corresponding eight-membered ring fused PAHs. The halogen-radical ring opening prob-ably occurs via a selective formation of a bis-allyl radical at the 1,3-cyclohexadiene moiety, halogenation at the bridgehead carbon and final electrocyclic ring opening.

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NOTICE: This is the peer reviewed version of the following article: Bello-García, J., Padín, D., Varela, J. A., Saá, C. (2021). Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes. Org. Lett., 23, 14, 5539-5544. [doi: 10.1021/acs.orglett.1c01881]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archiving

Keywords

Cyclooctatetraenes| Dihydrobiphenylenes| COT-PAHs| Electrocyclic ring opening| Radical halogenation

Bibliographic citation

Bello-García, J., Padín, D., Varela, J. A., Saá, C. (2021). Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes. Org. Lett., 23, 14, 5539-5544

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This work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). J.B. thanks Xunta de Galicia for a pre-doctoral contract. We are also grateful to the CESGA (Xunta de Gali-cia) for computational time.

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© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)

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