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

Yanpin Liu; Chaohuang Chen; Huaifeng Li; Kuo-Wei Huang; Jianwei Tan; Zhiqiang Weng

doi:10.1021/om4008967

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

Yanpin Liu, Chaohuang Chen, Huaifeng Li, Kuo-Wei Huang, Jianwei Tan, Zhiqiang Weng

Research output: Contribution to journal › Article › peer-review

45 Scopus citations

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.

Original language	English (US)
Pages (from-to)	6587-6592
Number of pages	6
Journal	Organometallics
Volume	32
Issue number	21
DOIs	https://doi.org/10.1021/om4008967
State	Published - Oct 18 2013

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: 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.

ASJC Scopus subject areas

Organic Chemistry
Physical and Theoretical Chemistry
Inorganic Chemistry

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10.1021/om4008967

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

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. {\textcopyright} 2013 American Chemical Society.",

author = "Yanpin Liu and Chaohuang Chen and Huaifeng Li and Kuo-Wei Huang and Jianwei Tan and Zhiqiang Weng",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.",

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doi = "10.1021/om4008967",

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T1 - Efficient SN2 fluorination of primary and secondary alkyl bromides by copper(I) fluoride complexes

AU - Liu, Yanpin

AU - Chen, Chaohuang

AU - Li, Huaifeng

AU - Huang, Kuo-Wei

AU - Tan, Jianwei

AU - Weng, Zhiqiang

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: 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.

PY - 2013/10/18

Y1 - 2013/10/18

N2 - 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.

AB - 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.

UR - http://hdl.handle.net/10754/563082

UR - https://pubs.acs.org/doi/10.1021/om4008967

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U2 - 10.1021/om4008967

DO - 10.1021/om4008967

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SN - 0276-7333

VL - 32

SP - 6587

EP - 6592

JO - Organometallics

JF - Organometallics

IS - 21

ER -

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

Abstract

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CCDC 949811: Experimental Crystal Structure Determination : bis(2,9-Dimethyl-1,10-phenanthroline)-copper hydrogen difluoride monohydrate

CCDC 949812: Experimental Crystal Structure Determination : Fluoro-(2,9-di-t-butyl-1,10-phenanthroline)-copper(i) triethylamine tris(hydrogen fluoride)

CCDC 949813: Experimental Crystal Structure Determination : (2,9-Di-t-butyl-1,10-phenanthroline)-bis(hydrogen fluoride)-copper

Cite this

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

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 949811: Experimental Crystal Structure Determination : bis(2,9-Dimethyl-1,10-phenanthroline)-copper hydrogen difluoride monohydrate

CCDC 949812: Experimental Crystal Structure Determination : Fluoro-(2,9-di-t-butyl-1,10-phenanthroline)-copper(i) triethylamine tris(hydrogen fluoride)

CCDC 949813: Experimental Crystal Structure Determination : (2,9-Di-t-butyl-1,10-phenanthroline)-bis(hydrogen fluoride)-copper

Cite this