RT Journal Article
T1 Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes
A1 Bello García, Jesús
A1 Padín Santos, Damián
A1 Varela Carrete, Jesús Ángel
A1 Saá Rodríguez, Carlos
K1 Cyclooctatetraenes
K1 Dihydrobiphenylenes
K1 COT-PAHs
K1 Electrocyclic ring opening
K1 Radical halogenation
AB 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.
PB American Chemical Society
SN 1523-7060
YR 2021
FD 2021
LK http://hdl.handle.net/10347/26643
UL http://hdl.handle.net/10347/26643
LA eng
NO 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
NO 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
NO 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.
DS Minerva
RD 28 abr 2026