An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides

Zhiqiang Weng; Weiming He; Chaohuang Chen; Richmond Lee; Davin Tan; Zhiping Lai; Dedao Kong; Yaofeng Yuan; Kuo-Wei Huang

doi:10.1002/anie.201208432

An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides

Zhiqiang Weng, Weiming He, Chaohuang Chen, Richmond Lee, Davin Tan, Zhiping Lai, Dedao Kong, Yaofeng Yuan, Kuo-Wei Huang

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

242 Scopus citations

Abstract

A series of copper(I) trifluoromethyl thiolate complexes have been synthesized from the reaction of CuF2 with Me3SiCF 3 and S8 (see scheme; Cu red, F green, N blue, S yellow). These air-stable complexes serve as reagents for the efficient conversion of a wide range of aryl halides into the corresponding aryl trifluoromethyl thioethers in excellent yields. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	1548-1552
Number of pages	5
Journal	Angewandte Chemie International Edition
Volume	52
Issue number	5
DOIs	https://doi.org/10.1002/anie.201208432
State	Published - Dec 12 2012

ASJC Scopus subject areas

Chemistry(all)
Catalysis

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10.1002/anie.201208432

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CCDC 900613: Experimental Crystal Structure Determination : bis(mu~2~-trifluoromethanethiolato)-bis(1,10-phenanthroline)-di-copper
Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Lee, R. (Creator), Tan, D. (Creator), Lai, Z. (Creator), Kong, D. (Creator), Yuan, Y. (Creator), Huang, K. (Creator), Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Kong, D. (Creator) & Yuan, Y. (Creator), Cambridge Crystallographic Data Centre, Mar 26 2014
DOI: 10.5517/ccz751d, http://hdl.handle.net/10754/624750
Dataset
CCDC 900612: Experimental Crystal Structure Determination : (4,4'-Di-t-butyl-2,2'-bipyridine)-trifluoromethanethiolato-copper
Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Lee, R. (Creator), Tan, D. (Creator), Lai, Z. (Creator), Kong, D. (Creator), Yuan, Y. (Creator), Huang, K. (Creator), Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Kong, D. (Creator) & Yuan, Y. (Creator), Cambridge Crystallographic Data Centre, Mar 26 2014
DOI: 10.5517/ccz750c, http://hdl.handle.net/10754/624749
Dataset
CCDC 900614: Experimental Crystal Structure Determination : bis(mu~2~-trifluoromethanethiolato)-bis(2,9-dimethyl-1,10-phenanthroline)-di-copper
Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Lee, R. (Creator), Tan, D. (Creator), Lai, Z. (Creator), Kong, D. (Creator), Yuan, Y. (Creator), Huang, K. (Creator), Weng, Z. (Creator), He, W. (Creator), Chen, C. (Creator), Kong, D. (Creator) & Yuan, Y. (Creator), Cambridge Crystallographic Data Centre, Mar 26 2014
DOI: 10.5517/ccz752f, http://hdl.handle.net/10754/624751
Dataset

Cite this

@article{4e0af2956ffb45b59ca7e01edb7e94ef,

title = "An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides",

abstract = "A series of copper(I) trifluoromethyl thiolate complexes have been synthesized from the reaction of CuF2 with Me3SiCF 3 and S8 (see scheme; Cu red, F green, N blue, S yellow). These air-stable complexes serve as reagents for the efficient conversion of a wide range of aryl halides into the corresponding aryl trifluoromethyl thioethers in excellent yields. Copyright {\textcopyright} 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Zhiqiang Weng and Weiming He and Chaohuang Chen and Richmond Lee and Davin Tan and Zhiping Lai and Dedao Kong and Yaofeng Yuan and Kuo-Wei Huang",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Prof. John Hartwig for useful discussions. The financial support from National Natural Science Foundation of China (21072030) and Fuzhou University (022318) to Z.W. and KAUST to K.-W.H. are acknowledged.",

year = "2012",

month = dec,

day = "12",

doi = "10.1002/anie.201208432",

language = "English (US)",

volume = "52",

pages = "1548--1552",

journal = "Angewandte Chemie International Edition",

issn = "1433-7851",

publisher = "John Wiley and Sons Ltd",

number = "5",

}

An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides. / Weng, Zhiqiang; He, Weiming; Chen, Chaohuang; Lee, Richmond; Tan, Davin; Lai, Zhiping; Kong, Dedao; Yuan, Yaofeng; Huang, Kuo-Wei.

In: Angewandte Chemie International Edition, Vol. 52, No. 5, 12.12.2012, p. 1548-1552.

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

TY - JOUR

T1 - An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides

AU - Weng, Zhiqiang

AU - He, Weiming

AU - Chen, Chaohuang

AU - Lee, Richmond

AU - Tan, Davin

AU - Lai, Zhiping

AU - Kong, Dedao

AU - Yuan, Yaofeng

AU - Huang, Kuo-Wei

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We thank Prof. John Hartwig for useful discussions. The financial support from National Natural Science Foundation of China (21072030) and Fuzhou University (022318) to Z.W. and KAUST to K.-W.H. are acknowledged.

PY - 2012/12/12

Y1 - 2012/12/12

N2 - A series of copper(I) trifluoromethyl thiolate complexes have been synthesized from the reaction of CuF2 with Me3SiCF 3 and S8 (see scheme; Cu red, F green, N blue, S yellow). These air-stable complexes serve as reagents for the efficient conversion of a wide range of aryl halides into the corresponding aryl trifluoromethyl thioethers in excellent yields. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - A series of copper(I) trifluoromethyl thiolate complexes have been synthesized from the reaction of CuF2 with Me3SiCF 3 and S8 (see scheme; Cu red, F green, N blue, S yellow). These air-stable complexes serve as reagents for the efficient conversion of a wide range of aryl halides into the corresponding aryl trifluoromethyl thioethers in excellent yields. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/562457

UR - http://doi.wiley.com/10.1002/anie.201208432

UR - http://www.scopus.com/inward/record.url?scp=84872845186&partnerID=8YFLogxK

U2 - 10.1002/anie.201208432

DO - 10.1002/anie.201208432

M3 - Article

C2 - 23239429

VL - 52

SP - 1548

EP - 1552

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 5

ER -

An air-stable copper reagent for nucleophilic trifluoromethylthiolation of aryl halides

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

CCDC 900613: Experimental Crystal Structure Determination : bis(mu~2~-trifluoromethanethiolato)-bis(1,10-phenanthroline)-di-copper

CCDC 900612: Experimental Crystal Structure Determination : (4,4'-Di-t-butyl-2,2'-bipyridine)-trifluoromethanethiolato-copper

CCDC 900614: Experimental Crystal Structure Determination : bis(mu~2~-trifluoromethanethiolato)-bis(2,9-dimethyl-1,10-phenanthroline)-di-copper

Cite this