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

272 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

General Chemistry
Catalysis

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10.1002/anie.201208432

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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.",

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month = dec,

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doi = "10.1002/anie.201208432",

language = "English (US)",

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pages = "1548--1552",

journal = "Angewandte Chemie International Edition",

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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

SN - 1433-7851

VL - 52

SP - 1548

EP - 1552

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 5

ER -

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

Abstract

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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

CCDC 900611: Experimental Crystal Structure Determination : catena-((mu~2~-trifluoromethanethiolato)-(2,2'-bipyridine)-copper)

Cite this

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

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

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Datasets

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

CCDC 900611: Experimental Crystal Structure Determination : catena-((mu~2~-trifluoromethanethiolato)-(2,2'-bipyridine)-copper)

Cite this