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dc.contributor.authorXu, Jun
dc.contributor.authorShen, Chao
dc.contributor.authorZhu, Xiaolei
dc.contributor.authorZhang, Pengfei
dc.contributor.authorAjitha, Manjaly John
dc.contributor.authorHuang, Kuo-Wei
dc.contributor.authorAn, Zhongfu
dc.contributor.authorLiu, Xiaogang
dc.date.accessioned2016-11-03T13:23:15Z
dc.date.available2016-11-03T13:23:15Z
dc.date.issued2016-02-04
dc.identifier.citationXu J, Shen C, Zhu X, Zhang P, Ajitha MJ, et al. (2016) Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling. Chemistry - An Asian Journal 11: 882–892. Available: http://dx.doi.org/10.1002/asia.201501407.
dc.identifier.issn1861-4728
dc.identifier.pmid26756288
dc.identifier.doi10.1002/asia.201501407
dc.identifier.urihttp://hdl.handle.net/10754/621709
dc.description.abstractAchieving site selectivity in carbon-hydrogen (C-H) functionalization reactions is a formidable challenge in organic chemistry. Herein, we report a novel approach to activating remote C-H bonds at the C5 position of 8-aminoquinoline through copper-catalyzed sulfonylation under mild conditions. Our strategy shows high conversion efficiency, a broad substrate scope, and good toleration with different functional groups. Furthermore, our mechanistic investigations suggest that a single-electron-transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C-S cross-coupling. Importantly, our copper-catalyzed remote functionalization protocol can be expanded for the construction of a variety of chemical bonds, including C-O, C-Br, C-N, C-C, and C-I. These findings provide a fundamental insight into the activation of remote C-H bonds, while offering new possibilities for rational design of drug molecules and optoelectronic materials requiring specific modification of functional groups. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
dc.description.sponsorshipWe thank the funding support from the National Natural Science Foundation of China (No. 21376058, 21302171), Zhejiang Provincial Natural Science Foundation of China (No. LZ13B 020001) and the Key-Sci-Tech Innovation Team of Zhejiang Province (No. 2010R50017).
dc.publisherWiley
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/asia.201501407/full
dc.subjectCross-coupling
dc.subjectRadicals
dc.subjectRemote C-H functionalization
dc.subjectSulfonylation
dc.titleRemote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling
dc.typeArticle
dc.contributor.departmentChemical Science Program
dc.contributor.departmentHomogeneous Catalysis Laboratory (HCL)
dc.contributor.departmentKAUST Catalysis Center (KCC)
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalChemistry - An Asian Journal
dc.contributor.institutionCollege of Material, Chemistry and Chemical Engineering; Hangzhou Normal University; Hangzhou 310036 China
dc.contributor.institutionCollege of Biology and Environmental Engineering; Zhejiang Shuren University; Hangzhou China
dc.contributor.institutionDepartment of Chemistry; National University of Singapore, 3 Science Drive 3; Singapore 117543 Singapore
kaust.personAjitha, Manjaly John
kaust.personHuang, Kuo-Wei
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc13z8r3
dc.relation.issupplementedbyDOI:10.5517/ccdc.csd.cc1jz9tm
display.relations<b> Is Supplemented By:</b> <br/> <ul><li><i>[Dataset]</i> <br/> Xu, J., Shen, C., Zhu, X., Zhang, P., Ajitha, M. J., Huang, K.-W., … Liu, X. (2016). CCDC 1041995: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc13z8r3. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc13z8r3">10.5517/ccdc.csd.cc13z8r3</a> HANDLE: <a href="http://hdl.handle.net/10754/624496">10754/624496</a></li><li><i>[Dataset]</i> <br/> Xu, J., Shen, C., Zhu, X., Zhang, P., Ajitha, M. J., Huang, K.-W., … Liu, X. (2016). CCDC 1429311: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccdc.csd.cc1jz9tm. DOI: <a href="https://doi.org/10.5517/ccdc.csd.cc1jz9tm">10.5517/ccdc.csd.cc1jz9tm</a> HANDLE: <a href="http://hdl.handle.net/10754/624525">10754/624525</a></li></ul>
dc.date.published-online2016-02-04
dc.date.published-print2016-03-18


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