Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

Handle URI:
http://hdl.handle.net/10754/621709
Title:
Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling
Authors:
Xu, Jun; Shen, Chao; Zhu, Xiaolei; Zhang, Pengfei; Ajitha, Manjaly John; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; An, Zhongfu; Liu, Xiaogang ( 0000-0003-2517-5790 )
Abstract:
Achieving 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.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division
Citation:
Xu 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.
Publisher:
Wiley-Blackwell
Journal:
Chemistry - An Asian Journal
Issue Date:
12-Jan-2016
DOI:
10.1002/asia.201501407
Type:
Article
ISSN:
1861-4728
Sponsors:
We 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).
Is Supplemented By:
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:10.5517/ccdc.csd.cc13z8r3; HANDLE:http://hdl.handle.net/10754/624496; 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:10.5517/ccdc.csd.cc1jz9tm; HANDLE:http://hdl.handle.net/10754/624525
Additional Links:
http://onlinelibrary.wiley.com/doi/10.1002/asia.201501407/full
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorXu, Junen
dc.contributor.authorShen, Chaoen
dc.contributor.authorZhu, Xiaoleien
dc.contributor.authorZhang, Pengfeien
dc.contributor.authorAjitha, Manjaly Johnen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorAn, Zhongfuen
dc.contributor.authorLiu, Xiaogangen
dc.date.accessioned2016-11-03T13:23:15Z-
dc.date.available2016-11-03T13:23:15Z-
dc.date.issued2016-01-12en
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.en
dc.identifier.issn1861-4728en
dc.identifier.doi10.1002/asia.201501407en
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.en
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).en
dc.publisherWiley-Blackwellen
dc.relation.urlhttp://onlinelibrary.wiley.com/doi/10.1002/asia.201501407/fullen
dc.subjectCross-couplingen
dc.subjectRadicalsen
dc.subjectRemote C-H functionalizationen
dc.subjectSulfonylationen
dc.titleRemote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Couplingen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalChemistry - An Asian Journalen
dc.contributor.institutionCollege of Material, Chemistry and Chemical Engineering; Hangzhou Normal University; Hangzhou 310036 Chinaen
dc.contributor.institutionCollege of Biology and Environmental Engineering; Zhejiang Shuren University; Hangzhou Chinaen
dc.contributor.institutionDepartment of Chemistry; National University of Singapore, 3 Science Drive 3; Singapore 117543 Singaporeen
kaust.authorAjitha, Manjaly Johnen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByXu, 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.cc13z8r3en
dc.relation.isSupplementedByDOI:10.5517/ccdc.csd.cc13z8r3en
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624496en
dc.relation.isSupplementedByXu, 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.cc1jz9tmen
dc.relation.isSupplementedByDOI:10.5517/ccdc.csd.cc1jz9tmen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624525en
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.