Efficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexes

Handle URI:
http://hdl.handle.net/10754/563082
Title:
Efficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexes
Authors:
Liu, Yanpin; Chen, Chaohuang; Li, Huaifeng ( 0000-0001-9661-803X ) ; Huang, Kuo-Wei ( 0000-0003-1900-2658 ) ; Tan, Jianwei; Weng, Zhiqiang
Abstract:
Copper(I) fluoride complexes ligated by phenanthroline derivatives have been synthesized and structurally characterized by X-ray crystallography. These complexes adopt as either ionic or neutral forms in the solid state, depending on the steric bulkiness of the substituent groups on the phenanthroline ligands. These complexes react with primary and secondary alkyl bromides to produce the corresponding alkyl fluorides in modest to good yields. This new method is compatible with a variety of important functional groups such as ether, thioether, amide, nitrile, methoxyl, hydroxyl, ketone, ester, and heterocycle moieties. © 2013 American Chemical Society.
KAUST Department:
KAUST Catalysis Center (KCC); Physical Sciences and Engineering (PSE) Division; Chemical Science Program; HCL
Publisher:
American Chemical Society (ACS)
Journal:
Organometallics
Issue Date:
11-Nov-2013
DOI:
10.1021/om4008967
Type:
Article
ISSN:
02767333
Sponsors:
We acknowledge the financial support from National Natural Science Foundation of China (21072030), Research Fund for the Doctoral Program of Higher Education of China (No. 20123514110003), SRF for ROCS, SEM (J20121707), the Science Foundation of the Fujian Province, China (2013J01040), and Fuzhou University (022318, 022494) to Z.W. and King Abdullah University of Science and Technology to K.-W.H.
Is Supplemented By:
Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949811: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc2b; DOI:10.5517/cc10wc2b; HANDLE:http://hdl.handle.net/10754/624240; Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949812: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc3c; DOI:10.5517/cc10wc3c; HANDLE:http://hdl.handle.net/10754/624241; Liu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949813: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc4d; DOI:10.5517/cc10wc4d; HANDLE:http://hdl.handle.net/10754/624242
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorLiu, Yanpinen
dc.contributor.authorChen, Chaohuangen
dc.contributor.authorLi, Huaifengen
dc.contributor.authorHuang, Kuo-Weien
dc.contributor.authorTan, Jianweien
dc.contributor.authorWeng, Zhiqiangen
dc.date.accessioned2015-08-03T11:35:22Zen
dc.date.available2015-08-03T11:35:22Zen
dc.date.issued2013-11-11en
dc.identifier.issn02767333en
dc.identifier.doi10.1021/om4008967en
dc.identifier.urihttp://hdl.handle.net/10754/563082en
dc.description.abstractCopper(I) fluoride complexes ligated by phenanthroline derivatives have been synthesized and structurally characterized by X-ray crystallography. These complexes adopt as either ionic or neutral forms in the solid state, depending on the steric bulkiness of the substituent groups on the phenanthroline ligands. These complexes react with primary and secondary alkyl bromides to produce the corresponding alkyl fluorides in modest to good yields. This new method is compatible with a variety of important functional groups such as ether, thioether, amide, nitrile, methoxyl, hydroxyl, ketone, ester, and heterocycle moieties. © 2013 American Chemical Society.en
dc.description.sponsorshipWe acknowledge the financial support from National Natural Science Foundation of China (21072030), Research Fund for the Doctoral Program of Higher Education of China (No. 20123514110003), SRF for ROCS, SEM (J20121707), the Science Foundation of the Fujian Province, China (2013J01040), and Fuzhou University (022318, 022494) to Z.W. and King Abdullah University of Science and Technology to K.-W.H.en
dc.publisherAmerican Chemical Society (ACS)en
dc.titleEfficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexesen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.contributor.departmentChemical Science Programen
dc.contributor.departmentHCLen
dc.identifier.journalOrganometallicsen
dc.contributor.institutionDepartment of Chemistry, Fuzhou University, Fujian 350108, Chinaen
kaust.authorLi, Huaifengen
kaust.authorHuang, Kuo-Weien
dc.relation.isSupplementedByLiu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949811: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc2ben
dc.relation.isSupplementedByDOI:10.5517/cc10wc2ben
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624240en
dc.relation.isSupplementedByLiu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949812: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc3cen
dc.relation.isSupplementedByDOI:10.5517/cc10wc3cen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624241en
dc.relation.isSupplementedByLiu, Y., Chen, C., Li, H., Huang, K.-W., Tan, J., & Weng, Z. (2014). CCDC 949813: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/cc10wc4den
dc.relation.isSupplementedByDOI:10.5517/cc10wc4den
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624242en
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