Synthesis of Phenanthrene-based Polycycles by Gold (I)-Catalyzed Cyclization of Biphenyl Embedded Trienynes
Authors
Milián López, Ana; García García, Patricia; Vaquero López, Juan José; Sanz, Roberto; Fernández Rodríguez, Manuel ÁngelIdentifiers
Permanent link (URI): http://hdl.handle.net/10017/59160DOI: 10.1002/adsc.202200887
ISSN: 1615-4150
Date
2022-09-14Funders
Ministerio de Ciencia e Innovación
Instituto de Salud Carlos III
Bibliographic citation
Advanced Synthesis and Catalysis, 2022, v. 364, n. 22, p. 3960-3966
Keywords
Phenanthrenes
Gold
Catalysis
Cycloisomerization
Trienynes
Project
info:eu-repo/grantAgreement/MICINN//PID2020-115128RB-I00/ES/
info:eu-repo/grantAgreement/ISCIII//RICORS2040%2FRD21%2F0005%2F0016/ES/
Document type
info:eu-repo/semantics/article
Version
info:eu-repo/semantics/publishedVersion
Rights
© The Authors
Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
Access rights
info:eu-repo/semantics/openAccess
Abstract
Gold(I)-catalyzed cyclization of o-alkenyl-o?-alkynylbiaryls in the presence of external or internal nucleophiles provides a straightforward access to phenanthrene-based polycycles, which are of considerable interest in materials science. Thus, their reactions with alcohols yield functionalized dihydrophenanthrenes, in a process that can also be carried out intramolecularly, to provide phenanthrene-derived heteropolycyclic compounds. Moreover, benzo[b]triphenylenes can be synthesized from o-methoxyvinyl-o?-alkynylbiaryls, in a reaction in which an (hetero)aryl substituent at the triple bond acts as an internal nucleophile.
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