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

Type
Article
Authors
Liu, Yanpin
Chen, Chaohuang
Li, Huaifeng cc
Huang, Kuo-Wei cc
Tan, Jianwei
Weng, Zhiqiang
KAUST Department
KAUST Catalysis Center (KCC)
Physical Sciences and Engineering (PSE) Division
Chemical Science Program
HCL
Date
2013-11-11

Metadata
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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.
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.
Publisher
American Chemical Society (ACS)
Journal
Organometallics
ISSN
02767333
DOI
10.1021/om4008967
Handle URI
http://hdl.handle.net/10754/563082
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
Collections
Articles; Physical Sciences and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)