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

[Image: see text] 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 (bCOT’s). Cross-couplings and Diels–Alder reactions of the bromi...

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Autores principales: Bello-García, Jesús, Padín, Damián, Varela, Jesús A., Saá, Carlos
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499027/
https://www.ncbi.nlm.nih.gov/pubmed/34228464
http://dx.doi.org/10.1021/acs.orglett.1c01881
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author Bello-García, Jesús
Padín, Damián
Varela, Jesús A.
Saá, Carlos
author_facet Bello-García, Jesús
Padín, Damián
Varela, Jesús A.
Saá, Carlos
author_sort Bello-García, Jesús
collection PubMed
description [Image: see text] 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 (bCOT’s). Cross-couplings and Diels–Alder reactions of the brominated bCOT’s allow the formation of the corresponding eight-membered ring-fused PAH’s. The halogen-radical ring opening probably occurs via a selective formation of a bis-allyl radical at the 1,3-cyclohexadiene moiety, halogenation at the bridgehead carbon, and finally electrocyclic ring opening.
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spelling pubmed-84990272021-10-12 Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes Bello-García, Jesús Padín, Damián Varela, Jesús A. Saá, Carlos Org Lett [Image: see text] 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 (bCOT’s). Cross-couplings and Diels–Alder reactions of the brominated bCOT’s allow the formation of the corresponding eight-membered ring-fused PAH’s. The halogen-radical ring opening probably occurs via a selective formation of a bis-allyl radical at the 1,3-cyclohexadiene moiety, halogenation at the bridgehead carbon, and finally electrocyclic ring opening. American Chemical Society 2021-07-06 2021-07-16 /pmc/articles/PMC8499027/ /pubmed/34228464 http://dx.doi.org/10.1021/acs.orglett.1c01881 Text en © 2021 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Bello-García, Jesús
Padín, Damián
Varela, Jesús A.
Saá, Carlos
Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title_full Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title_fullStr Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title_full_unstemmed Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title_short Nonplanar Tub-Shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
title_sort nonplanar tub-shaped benzocyclooctatetraenes via halogen-radical ring opening of dihydrobiphenylenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8499027/
https://www.ncbi.nlm.nih.gov/pubmed/34228464
http://dx.doi.org/10.1021/acs.orglett.1c01881
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