Metal-Free Temperature-Controlled Regiodivergent Borylative Cyclizations of Enynes: BCl3-Promoted Skeletal Rearrangement
Authors
Milián López, Ana; Fernández Rodríguez, Manuel Ángel; Merino Marcos, Estíbaliz; Vaquero López, Juan José; García Gallego, PatriciaIdentifiers
Permanent link (URI): http://hdl.handle.net/10017/59157DOI: 10.1002/anie.202205651
ISSN: 0570-0833
Date
2022Funders
Ministerio de Ciencia e Innovación
Instituto de Salud Carlos III
Comunidad de Madrid
Bibliographic citation
Angewandte Chemie - International Edition in English, 2022, v. 61, n. 28 (E202205651), p. 1-6
Keywords
Boron
Cyclization
Enynes
Phenanthrenes
Rearrangement
Project
info:eu-repo/grantAgreement/MICINN//PID2020-115128RB-I00/ES/
info:eu-repo/grantAgreement/ISCIII//RICORS2040%2FRD21%2F0005%2F0016/ES/
info:eu-repo/grantAgreement/CAM//2018-T1%2FIND-10054/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
Metal-free borylative cyclization of biphenylembedded 1,3,5-trien-7-ynes in the presence of simple and inexpensive BCl3 provided synthetically useful borylated building blocks. The outcome of the process depends on the reaction temperature, with borylated phenanthrenes obtained at 60 °C and phenanthrenefused borylated cyclobutanes formed at 0°C. Based on DFT calculations, a mechanism for these novel transformations has been proposed, which involves an uncommon skeletal rearrangement, including migration of a methyl group and alkyne fragmentation, unprecedented in BCl3-promoted cyclization reactions
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Metal_Milian_AngChem_2022.pdf | 3.968Mb |
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