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Formation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones.

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dc.contributor.authorYu, Guojun
dc.contributor.authorClive, Derrick L. J.
dc.date.accessioned2025-05-01T12:10:55Z
dc.date.available2025-05-01T12:10:55Z
dc.date.issued2016-01-01
dc.descriptionAddition of Grignard- or other organometallic reagents to 3-halocyclohex-2-en- 1-ones bearing an alkyl or aryl group at C-5, followed by mild acid treatment and exposure to DBU at room temperature, generates meta-substituted phenols in which the newly introduced meta substituent originates from the Grignard reagent. The range of effective organometallic reagents includes alkyl, allyl, alkynyl, aryl and heteroaryl compounds including those with fluorine substituents. The initial halocyclohexenone can be deprotonated at C-6 and reacted with carbon, fluorine or sulfur electrophiles before the Grignard addition so as to generate highly substituted phenols.
dc.identifier.doihttps://doi.org/10.7939/r3-jesq-g504
dc.language.isoen
dc.relation.isversionofYu, G., & Clive, D. L. J. (2016). Formation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones. Journal of Organic Chemistry, 81(18), 8470–8484. https://doi-org.login.ezproxy.library.ualberta.ca/10.1021/acs.joc.6b01653
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in Journal of Organic Chemistry, copyright © 2016 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.joc.6b01653.
dc.subjectEnantioselective TOtal-Synthesis
dc.subjectMagnetic-Resonance
dc.subjectDerivatives
dc.subjectCyclohexenones
dc.subjectCyclization
dc.subjectReagents
dc.subjectRing
dc.subjectPRecursosrs
dc.subjectEthers
dc.subjectLICL
dc.titleFormation of meta-Substituted Phenols by Transition Metal-Free Aromatization: Use of 2-Bromocyclohex-2-en-1-ones.
dc.typehttp://purl.org/coar/resource_type/c_6501 http://purl.org/coar/version/c_b1a7d7d4d402bcce http://purl.org/coar/version/c_71e4c1898caa6e32
ual.jupiterAccesshttp://terms.library.ualberta.ca/public

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