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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.accessioned2015-11-12T21:04:02Z
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 International Edition 54(43): 12683-12686.en_US
dc.identifier.issn1433-7851en_US
dc.identifier.issn1521-3773en_US
dc.identifier.urihttps://hdl.handle.net/2027.42/115938
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.A Cu and Ag sequence: The bis‐functionalization of styrenes is accomplished through a copper‐catalyzed process that enables hydroboration of the alkene and regioselective ortho cyanation of the arene. The resulting adducts are converted, by a radical cyclization process, into a cyclopentanone unit fused to the original aromatic ring. Together, these methods allow efficient cyclopentannulation of a broad range of styrene derivatives.en_US
dc.publisherWILEY‐VCH Verlagen_US
dc.subject.otherradicalsen_US
dc.subject.otherannulationsen_US
dc.subject.othersilveren_US
dc.subject.othercopperen_US
dc.subject.othercyclizationsen_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.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/2027.42/115938/1/anie_201507303_sm_miscellaneous_information.pdf
dc.description.bitstreamurlhttp://deepblue.lib.umich.edu/bitstream/2027.42/115938/2/12683_ftp.pdf
dc.identifier.doi10.1002/anie.201507303en_US
dc.identifier.sourceAngewandte Chemie International Editionen_US
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