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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 1
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Original Articles

L‐Proline‐Promoted CuI‐Catalyzed C‐S Bond Formation between Aryl Iodides and Thiols

Hui Zhang Department of Chemistry, Shanghai University, Shanghai, ChinaCorrespondence[email protected]
,
Weiguo Cao Department of Chemistry, Shanghai University, Shanghai, China; State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, China
&
Dawei Ma State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, Shanghai, China
Pages 25-35 | Received 12 May 2006, Published online: 25 Jul 2007

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Hao Lin & Dianqing Sun. (2013) Recent Synthetic Developments and Applications of the Ullmann Reaction. A Review. Organic Preparations and Procedures International 45:5, pages 341-394.
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Xin-Yan Zhang, Xiao-Yan Zhang & Sheng-Rong Guo. (2011) Efficient copper(I)-catalyzed C–S cross-coupling of thiols with aryl halides in an aqueous two-phase system. Journal of Sulfur Chemistry 32:1, pages 23-35.
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K.S. Sindhu, Amrutha P. Thankachan, Anns Maria Thomas & Gopinathan Anilkumar. (2015) An efficient iron-catalyzed S-arylation of aryl and alkylthiols with aryl halides in the presence of water under aerobic conditions. Tetrahedron Letters 56:34, pages 4923-4926.
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Debasish Kundu, Manisha Tripathy, Pintu Maity & Brindaban C. Ranu. (2015) Cobalt-Catalyzed Intermolecular C(sp 2 )O Cross-Coupling . Chemistry - A European Journal 21:24, pages 8727-8732.
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Amrutha P. Thankachan, K. S. Sindhu, K. Keerthi Krishnan & Gopinathan Anilkumar. (2015) A novel and efficient zinc-catalyzed thioetherification of aryl halides. RSC Advances 5:41, pages 32675-32678.
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Chin-Yiu Chan, Yi-Chun Wong, Mei-Yee Chan, Sin-Hang Cheung, Shu-Kong So & Vivian Wing-Wah Yam. (2014) Hole-Transporting Spirothioxanthene Derivatives as Donor Materials for Efficient Small-Molecule-Based Organic Photovoltaic Devices. Chemistry of Materials 26:22, pages 6585-6594.
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Wei-Sheng Huang, Rongsong Xu, Rory Dodd & William C. Shakespeare. (2013) Facile synthesis of 1,4-benzothiazin-3-ones from Cu-catalyzed coupling of 2-iodoanilines and 2-mercaptoacetate. Tetrahedron Letters 54:38, pages 5214-5216.
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Gordon W. Gribble, Liangfeng Fu & Qi-Xian Lin. 2013. Pyridines: from lab to production. Pyridines: from lab to production 153 373 .
Sanny Verma, Neeraj Kumar & Suman L. Jain. (2012) Copper(II) trans-bis-(glycinato): an efficient heterogeneous catalyst for cross coupling of phenols with aryl halides. Tetrahedron Letters 53:35, pages 4665-4668.
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Hua-Jian Xu, Yu-Feng Liang, Xin-Feng Zhou & Yi-Si Feng. (2012) Efficient recyclable CuI-nanoparticle-catalyzed S-arylation of thiols with aryl halides on water under mild conditions. Organic & Biomolecular Chemistry 10:13, pages 2562.
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Akhilesh Kumar Verma. 2012. Advances in Heterocyclic Chemistry Volume 107. Advances in Heterocyclic Chemistry Volume 107 101 132 .
Shuji Yasuike, Motokazu Nishioka, Naoki Kakusawa & Jyoji Kurita. (2011) Simple and efficient copper-catalyzed S-arylation of diaryl disulfides with triarylbismuthanes under aerobic conditions. Tetrahedron Letters 52:48, pages 6403-6406.
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Hsin-Lun Kao & Chin-Fa Lee. (2011) Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides. Organic Letters 13:19, pages 5204-5207.
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Sandeep M. Agawane & Jayashree M. Nagarkar. (2011) Nano ceria catalyzed Ullmann type coupling reactions. Tetrahedron Letters 52:41, pages 5220-5223.
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Juntae Mo, Dahan Eom, Sung Hong Kim & Phil Ho Lee. (2011) Palladium-catalyzed Carbon–Sulfur Cross-coupling Reactions of Aryl Chlorides with Indium Tris(organothiolates). Chemistry Letters 40:9, pages 980-982.
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Christopher B. Kelly, Christopher (Xiang) Lee & Nicholas E. Leadbeater. (2011) Copper-catalyzed direct preparation of diaryl sulfides from aryl iodides using potassium thiocyanate as a sulfur transfer reagent. Tetrahedron Letters 52:36, pages 4587-4589.
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Irina P. Beletskaya & Valentine P. Ananikov. (2011) Transition-Metal-Catalyzed C−S, C−Se, and C−Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions. Chemical Reviews 111:3, pages 1596-1636.
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Phil Ho Lee, Youngchul Park, Sangkyun Park, Euijae Lee & Sunggak Kim. (2011) Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure. The Journal of Organic Chemistry 76:3, pages 760-765.
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Chad C. Eichman & James P. Stambuli. (2011) Transition Metal Catalyzed Synthesis of Aryl Sulfides. Molecules 16:1, pages 590-608.
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Zvi RappoportLiza Penn & Dmitri Gelman. 2010. Patai's Chemistry of Functional Groups. Patai's Chemistry of Functional Groups.
Jingli Xie, Stuart R. Batten, Yang Zou & Xiaoming Ren. (2010) Observation of in Situ Ligand Reactions during the Assembly of Crystalline Zn−S Clusters. Crystal Growth & Design 11:1, pages 16-20.
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Ming-Tzu Lan, Wei-Yi Wu, Shao-Hsien Huang, Kai-Luen Luo & Fu-Yu Tsai. (2011) Reusable and efficient CoCl2·6H2O/cationic 2,2’-bipyridyl system-catalyzed S-arylation of aryl halides with thiols in water under air. RSC Advances 1:9, pages 1751.
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Adri van den Hoogenband, Jos H.M. Lange, Raymond P.J. Bronger, Axel R. Stoit & Jan Willem Terpstra. (2010) A simple, base-free preparation of S-aryl thioacetates as surrogates for aryl thiols. Tetrahedron Letters 51:52, pages 6877-6881.
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Yongwen Jiang & Dawei Ma. 2010. Catalysis without Precious Metals. Catalysis without Precious Metals 213 233 .
Yogesh Goriya & C.V. Ramana. (2010) The [Cu]-catalyzed SNAR reactions: direct amination of electron deficient aryl halides with sodium azide and the synthesis of arylthioethers under Cu(II)–ascorbate redox system. Tetrahedron 66:38, pages 7642-7650.
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M. Shahjahan Kabir, Michael Lorenz, Michael L. Van Linn, Ojas A. Namjoshi, Shamim Ara & James M. Cook. (2010) A Very Active Cu-Catalytic System for the Synthesis of Aryl, Heteroaryl, and Vinyl Sulfides. The Journal of Organic Chemistry 75:11, pages 3626-3643.
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Zhongyu Duan, Sadananda Ranjit & Xiaogang Liu. (2010) One-Pot Synthesis of Amine-Substituted Aryl Sulfides and Benzo[ b ]thiophene Derivatives . Organic Letters 12:10, pages 2430-2433.
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Huifeng Wang, Linlin Jiang, Tao Chen & Yaming Li. (2010) A Highly Efficient, Ligand‐Free, and Recyclable Cu 2 S‐Catalyzed Coupling of Aryl Iodides with Diaryl Disulfides . European Journal of Organic Chemistry 2010:12, pages 2324-2329.
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Dawei Ma, Qian Geng, Hui Zhang & Yongwen Jiang. (2010) Assembly of Substituted Phenothiazines by a Sequentially Controlled CuI/  L ‐Proline‐Catalyzed Cascade CS and CN Bond Formation . Angewandte Chemie International Edition 49:7, pages 1291-1294.
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Dawei Ma, Qian Geng, Hui Zhang & Yongwen Jiang. (2010) Assembly of Substituted Phenothiazines by a Sequentially Controlled CuI/  L ‐Proline‐Catalyzed Cascade CS and CN Bond Formation . Angewandte Chemie 122:7, pages 1313-1316.
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Paul Bichler & Jennifer A. Love. 2010. C-X Bond Formation. C-X Bond Formation 39 64 .
Jan Krouželka & Igor Linhart. (2009) Preparation of Arylmercapturic Acids by S ‐Arylation of N , N ′‐Diacetylcystine . European Journal of Organic Chemistry 2009:36, pages 6336-6340.
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Yongwen Jiang, Yuxia Qin, Siwei Xie, Xiaojing Zhang, Jinhua Dong & Dawei Ma. (2009) A General and Efficient Approach to Aryl Thiols: CuI-Catalyzed Coupling of Aryl Iodides with Sulfur and Subsequent Reduction. Organic Letters 11:22, pages 5250-5253.
Crossref
Yang Feng, Huifeng Wang, Fangfang Sun, Yaming Li, Xinmei Fu & Kun Jin. (2009) A highly efficient and widely functional-group-tolerant catalyst system for copper(I)-catalyzed S-arylation of thiols with aryl halides. Tetrahedron 65:47, pages 9737-9741.
Crossref
Zheng Jiang, Jin She & Xufeng Lin. (2009) Palladium on Charcoal as a Recyclable Catalyst for CS Cross‐Coupling of Thiols with Aryl Halides under Ligand‐Free Conditions. Advanced Synthesis & Catalysis 351:16, pages 2558-2562.
Crossref
Qian Geng, Hui Zhang, Weiguo Cao & Yali Chen. (2009) A Facile Synthesis of N ‐Aryl Substituted Piperidones . Chinese Journal of Chemistry 27:10, pages 1995-2000.
Crossref
Sukalyan Bhadra, Bojja Sreedhar & Brindaban C. Ranu. (2009) Recyclable Heterogeneous Supported Copper‐Catalyzed Coupling of Thiols with Aryl Halides: Base‐Controlled Differential Arylthiolation of Bromoiodobenzenes. Advanced Synthesis & Catalysis 351:14-15, pages 2369-2378.
Crossref
Jiangang Gan & Dawei Ma. (2009) Synthesis of 1,5-Benzothiazepine Dipeptide Mimetics via Two CuI-Catalyzed Cross Coupling Reactions. Organic Letters 11:13, pages 2788-2790.
Crossref
D.J.C. Prasad, Ajay B. Naidu & G. Sekar. (2009) An efficient intermolecular C(aryl)–S bond forming reaction catalyzed by BINAM–copper(II) complex. Tetrahedron Letters 50:13, pages 1411-1415.
Crossref
Jin She, Zheng Jiang & Yanguang Wang. (2009) Simple, efficient and recyclable catalytic system for performing copper-catalyzed C–S coupling of thiols with aryl iodides in PEG and PEG–H2O. Tetrahedron Letters 50:5, pages 593-596.
Crossref
María Teresa Herrero, Raul SanMartin & Esther Domínguez. (2009) Copper(I)-catalyzed S-arylation of thiols with activated aryl chlorides on water. Tetrahedron 65:7, pages 1500-1503.
Crossref
Qiwu Zhao, Ling Li, Yewen Fang, Deqian Sun & Chaozhong Li. (2008) “Ligand-Free” CuI-Catalyzed Highly Efficient Intramolecular S-Vinylation of Thiols with Vinyl Chlorides and Bromides. The Journal of Organic Chemistry 74:1, pages 459-462.
Crossref
Wei-Yi Wu, Jui-Chan Wang & Fu-Yu Tsai. (2009) A reusable FeCl3·6H2O/cationic 2,2′-bipyridyl catalytic system for the coupling of aryl iodides with thiols in water under aerobic conditions. Green Chemistry 11:3, pages 326.
Crossref
Chul-Hee Cho, Benjamin Neuenswander, Gerald H. Lushington & Richard C. Larock. (2008) Parallel Synthesis of a Multi-Substituted Benzo[ b ]furan Library . Journal of Combinatorial Chemistry 10:6, pages 941-947.
Crossref
Pongchart Buranaprasertsuk, Joyce Wei Wei Chang, Warinthorn Chavasiri & Philip Wai Hong Chan. (2008) Copper-catalyzed Ullmann coupling under ligand- and additive-free conditions. Part 2: S-Arylation of thiols with aryl iodides. Tetrahedron Letters 49:12, pages 2023-2025.
Crossref
Laxmidhar Rout, Prasenjit Saha, Suribabu Jammi & Tharmalingam Punniyamurthy. (2008) Efficient Copper(I)‐Catalyzed C–S Cross Coupling of Thiols with Aryl Halides in Water. European Journal of Organic Chemistry 2008:4, pages 640-643.
Crossref
Jinho Kim & Sukbok Chang. (2008) Ammonium salts as an inexpensive and convenient nitrogen source in the Cu-catalyzed amination of aryl halides at room temperature. Chemical Communications:26, pages 3052.
Crossref
Akhilesh Kumar Verma, Jaspal Singh & Ritu Chaudhary. (2007) A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols. Tetrahedron Letters 48:40, pages 7199-7202.
Crossref
Hui Zhang, Weiguo Cao & Dawei Ma. (2007) L‐Proline‐Promoted CuI‐Catalyzed C—S Bond Formation Between Aryl Iodides and Thiols.. ChemInform 38:25.
Crossref

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