Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls

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dc.citation.firstpage566en_US
dc.citation.issueNumber2en_US
dc.citation.journalTitleAngewandte Chemie International Editionen_US
dc.citation.lastpage571en_US
dc.citation.volumeNumber55en_US
dc.contributor.authorGao, Hongyinen_US
dc.contributor.authorXu, Qing-Longen_US
dc.contributor.authorKeene, Craigen_US
dc.contributor.authorYousufuddin, Muhammeden_US
dc.contributor.authorEss, Daniel H.en_US
dc.contributor.authorKürti, Lászlóen_US
dc.date.accessioned2017-05-23T19:32:18Z
dc.date.available2017-05-23T19:32:18Z
dc.date.issued2016en_US
dc.description.abstractAn organic acid catalyzed direct arylation of aromatic C(sp2)H bonds in phenols and naphthols for the preparation of 1,1′-linked functionalized biaryls was developed. The products are non-C2-symmetrical, atropoisomeric, and represent previously untapped chemical space. Overall this transformation is operationally simple, does not require an external oxidant, is readily scaled up (up to 98 mmol), and the structurally diverse 2,2′-dihydroxy biaryl (i.e., BINOL-type), as well as 2-amino-2′-hydroxy products (i.e., NOBIN-type) are formed with complete regioselectivity. Density-functional calculations suggest that the quinone and imino-quinone monoacetal coupling partners are exclusively arylated at their α-position by an asynchronous [3,3]-sigmatropic rearrangement of a mixed acetal species which is formed in situ under the reaction conditions.en_US
dc.identifier.citationGao, Hongyin, Xu, Qing-Long, Keene, Craig, et al.. "Practical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biaryls." <i>Angewandte Chemie International Edition,</i> 55, no. 2 (2016) Wiley: 566-571. https://doi.org/10.1002/anie.201508419.
dc.identifier.doihttps://doi.org/10.1002/anie.201508419en_US
dc.identifier.urihttps://hdl.handle.net/1911/94360
dc.language.isoengen_US
dc.publisherWiley
dc.rightsThis is an author's peer-reviewed final manuscript, as accepted by the publisher. The published article is copyrighted by Wiley.en_US
dc.subject.keywordtransition metal-freeen_US
dc.subject.keywordfunctionalized biarylsen_US
dc.subject.keywordatropoisomericen_US
dc.subject.keyworddirect arylationen_US
dc.subject.keywordorganocatalysisen_US
dc.subject.keywordquinone monoacetalsen_US
dc.titlePractical Organocatalytic Synthesis of Functionalized Non-C2-Symmetrical Atropisomeric Biarylsen_US
dc.typeJournal articleen_US
dc.type.dcmiTexten_US
dc.type.publicationpost-printen_US
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