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Functionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processes
dc.contributor.authorZhao, Wanxiangen_US
dc.contributor.authorMontgomery, Johnen_US
dc.date.accessioned2015-11-12T21:04:06Z
dc.date.available2016-12-01T14:33:05Zen
dc.date.issued2015-10-19en_US
dc.identifier.citationZhao, Wanxiang; Montgomery, John (2015). "Functionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processes." Angewandte Chemie 127(43): 12874-12877.en_US
dc.identifier.issn0044-8249en_US
dc.identifier.issn1521-3757en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/115946
dc.description.abstractAn efficient two‐step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2pin2) and N‐cyano‐N‐phenyl‐p‐methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cyanation of the benzene unit. The products thus obtained are further functionalized by a AgNO3/Selectfluor‐mediated coupling of the BPin and cyano functionalities to annulate a new five‐membered ring. This combined two‐step sequence provides a versatile method for the site‐selective derivatization of a broad range of vinyl arene substrates.Ein Cu‐ und Ag‐Sequenz: Die Difunktionalisierung von Styrolen gelingt durch einen Kupfer‐katalysierten Prozess, der die Hydroborierung des Alkens und die regioselektive ortho‐Cyanierung des Arens einschließt. Die entstehenden Addukte werden durch eine radikalische Cyclisierung mit Silber in ein am aromatischen Ring anelliertes Cyclopentanon umgewandelt.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherRadikaleen_US
dc.subject.otherSilberen_US
dc.subject.otherAnellierungenen_US
dc.subject.otherCyclisierungenen_US
dc.subject.otherKupferen_US
dc.titleFunctionalization of Styrenes by Copper‐Catalyzed Borylation/ ortho‐Cyanation and Silver‐Catalyzed Annulation Processesen_US
dc.typeArticleen_US
dc.rights.robotsIndexNoFollowen_US
dc.subject.hlbsecondlevelChemistryen_US
dc.subject.hlbsecondlevelMaterials Science and Engineeringen_US
dc.subject.hlbsecondlevelChemical Engineeringen_US
dc.subject.hlbtoplevelEngineeringen_US
dc.subject.hlbtoplevelScienceen_US
dc.description.peerreviewedPeer Revieweden_US
dc.contributor.affiliationumDepartment of Chemistry, University of Michigan, 930 N. University Ave, Ann Arbor, MI 48109‐1055 (USA) http://www.umich.edu/∼jmgroupen_US
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/115946/1/ange_201507303_sm_miscellaneous_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/115946/2/12874_ftp.pdf
dc.identifier.doi10.1002/ange.201507303en_US
dc.identifier.sourceAngewandte Chemieen_US
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dc.owningcollnameInterdisciplinary and Peer-Reviewed


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