Advanced search
Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 1
Submit an article Journal homepage
916
Views
73
CrossRef citations to date
0
Altmetric
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

Citations (73)

Keep up to date with the latest research on this topic with citation updates for this article.

Subscribe to citation updates

Read on this site (2)

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.
Read now
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.
Read now

Articles from other publishers (71)

Bapu R. Thorat, Suraj N. Mali, Swati S. Wavhal, Devidas S. Bhagat, Ravikumar M. Borade, A. Chapolikar, Ajaykumar Gandhi & Pawan Shinde. (2023) L-Proline: A Versatile Organo-Catalyst in Organic Chemistry. Combinatorial Chemistry & High Throughput Screening 26:6, pages 1108-1140.
Crossref
Navjeet Kaur. 2023. Iodine-Assisted Synthesis of Six- and Seven-Membered Heterocycles. Iodine-Assisted Synthesis of Six- and Seven-Membered Heterocycles 335 358 .
Vilija Kederienė, Jolanta Rousseau, Marie Schuler, Algirdas Šačkus & Arnaud Tatibouët. (2022) Copper-catalyzed S-arylation of Furanose-Fused Oxazolidine-2-thiones. Molecules 27:17, pages 5597.
Crossref
Partha Kumar Samanta, Rima Biswas, Samanka Narayan Bhaduri, Shounak Ray & Papu Biswas. (2021) Copper(0) nanoparticles immobilized on SBA-15: A versatile recyclable heterogeneous catalyst for solvent and ligand free C–S coupling reaction from diverse substrates. Microporous and Mesoporous Materials 323, pages 111198.
Crossref
Jing‐Ya Zhou & Yong‐Ming Zhu. (2021) Forging C−S(Se) Bonds by Nickel‐catalyzed Decarbonylation of Carboxylic Acid and Cleavage of Aryl Dichalcogenides. European Journal of Organic Chemistry 2021:17, pages 2452-2461.
Crossref
Dayun Huang & Xiangmei Wu. (2021) t-BuOK-promoted methylthiolation of aryl fluorides with dimethyldisulfide under transition-metal-free and mild conditions. Journal of Fluorine Chemistry 245, pages 109778.
Crossref
Tomáš Weidlich. (2021) The Influence of Copper on Halogenation/Dehalogenation Reactions of Aromatic Compounds and Its Role in the Destruction of Polyhalogenated Aromatic Contaminants. Catalysts 11:3, pages 378.
Crossref
Weigang Zhang, Mengjun Huang, Zhenlei Zou, Zhengguang Wu, Shengyang Ni, Lingyu Kong, Youxuan Zheng, Yi Wang & Yi Pan. (2021) Redox-active benzimidazolium sulfonamides as cationic thiolating reagents for reductive cross-coupling of organic halides. Chemical Science 12:7, pages 2509-2514.
Crossref
Fengtian Wu. (2020) The synthesis of N ‐containing heterocyclic compounds catalyzed by copper/ L ‐proline . Applied Organometallic Chemistry 34:12.
Crossref
A. V. Murashkina, A. Yu. Mitrofanov & I. P. Beletskaya. (2020) Copper in Cross-Coupling Reactions: II. Arylation of Thiols. Russian Journal of Organic Chemistry 55:11, pages 1629-1641.
Crossref
Sara S. E. Ghodsinia & Batool Akhlaghinia. (2019) Cu I anchored onto mesoporous SBA-16 functionalized by aminated 3-glycidyloxypropyltrimethoxysilane with thiosemicarbazide (SBA-16/GPTMS-TSC-Cu I ): a heterogeneous mesostructured catalyst for S -arylation reaction under solvent-free conditions . Green Chemistry 21:11, pages 3029-3049.
Crossref
Prabusankar Ganesan, Adinarayana Mannem & Nirmala Muthukumaran. (2019) Anionic Bismuth(III) chloride cluster with diselenide countercations: Application in C-S cross coupling reactions. Journal of Organometallic Chemistry 884, pages 29-35.
Crossref
K.S. Sindhu, T.G. Abi, George Mathai & Gopinathan Anilkumar. (2019) An efficient protocol for the synthesis of thioethers via iron-catalyzed cross-coupling reaction and its mechanistic investigation. Polyhedron 158, pages 270-276.
Crossref
Tony Garnier, Mathieu Danel, Valentin Magné, Anthony Pujol, Valérie Bénéteau, Patrick Pale & Stefan Chassaing. (2018) Copper(I)–USY as a Ligand-Free and Recyclable Catalyst for Ullmann-Type O -, N -, S -, and C -Arylation Reactions: Scope and Application to Total Synthesis . The Journal of Organic Chemistry 83:12, pages 6408-6422.
Crossref
Joydev K. Laha & Shubhra Sharma. (2018) Palladium-Catalyzed Intramolecular Oxidative Arylations for the Synthesis of Fused Biaryl Sulfones. ACS Omega 3:5, pages 4860-4870.
Crossref
Li Liu, Jian Qiang, Shuhua Bai, Yang Li & Jian Li. (2017) Iron‐catalyzed carbon–sulfur bond formation: Atom‐economic construction of thioethers with diaryliodonium salts. Applied Organometallic Chemistry 31:11.
Crossref
Wei Gao, Linchu Xu, Chun Gong, Qiuping Ding & Yiyuan Peng. (2017) An efficient route to 4-aryloxycoumarins via one-pot reactions of 4-hydroxycoumarins with hypervalent iodine reagents. Tetrahedron Letters 58:42, pages 4020-4023.
Crossref
Wei-Kai Huang, Wei-Ting Chen, I.-Jui Hsu, Chien-Chung Han & Shin-Guang Shyu. (2017) Cross C–S coupling reaction catalyzed by copper( i ) N-heterocyclic carbene complexes . RSC Advances 7:9, pages 4912-4920.
Crossref
Bianxiang Zhang, Yongqiang Kang, Lihua Yang & Xia Chen. (2016) A S-Arylation of 2-Mercaptoazoles with Diaryliodonium Triflates under Metal-Free and Base-Free Conditions. ChemistrySelect 1:8, pages 1529-1532.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
Ravinderpal Kour Sodhi, Avtar Changotra & Satya Paul. (2014) Metal Acetylacetonates Covalently Anchored onto Amine Functionalized Silica/Starch Composite for the One-Pot Thioetherification and Synthesis of 2H-Indazoles. Catalysis Letters 144:11, pages 1819-1831.
Crossref
Yanhong Liu, Lincheng Zhou, Xinping Hui, Zhenwen Dong, Hao Zhu, Yanming Shao & Yanfeng Li. (2014) Fabrication of magnetic amino-functionalized nanoparticles for S-arylation of heterocyclic thiols. RSC Adv. 4:90, pages 48980-48985.
Crossref
Mona Hosseini-Sarvari & Zahra Razmi. (2014) Highly active recyclable heterogeneous Pd/ZnO nanoparticle catalyst: sustainable developments for the C–O and C–N bond cross-coupling reactions of aryl halides under ligand-free conditions. RSC Adv. 4:83, pages 44105-44116.
Crossref
Hsing-Ying Chen, Wei-Te Peng, Ying-Hsien Lee, Yu-Lun Chang, Yen-Jen Chen, Yi-Chun Lai, Nai-Yuan Jheng & Hsuan-Ying Chen. (2013) Use of Base Control To Provide High Selectivity between Diaryl Thioether and Diaryl Disulfide for C–S Coupling Reactions of Aryl Halides and Sulfur and a Mechanistic Study. Organometallics 32:19, pages 5514-5522.
Crossref
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.
Crossref
Emir Hubijar, Alexios Papadimitratos, Doyun Lee, Anvar Zakhidov & John P. Ferraris. (2012) Synthesis and Characterization of a Novel Symmetrical Sulfone-Substituted Polyphenylene Vinylene (SO 2 EH-PPV) for Applications in Light Emitting Devices . The Journal of Physical Chemistry B 117:16, pages 4442-4448.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
Hsin-Lun Kao & Chin-Fa Lee. (2011) Efficient Copper-Catalyzed S-Vinylation of Thiols with Vinyl Halides. Organic Letters 13:19, pages 5204-5207.
Crossref
Sandeep M. Agawane & Jayashree M. Nagarkar. (2011) Nano ceria catalyzed Ullmann type coupling reactions. Tetrahedron Letters 52:41, pages 5220-5223.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
Chad C. Eichman & James P. Stambuli. (2011) Transition Metal Catalyzed Synthesis of Aryl Sulfides. Molecules 16:1, pages 590-608.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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.
Crossref
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

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Order Reprints Request Corporate Permissions

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

Request Academic Permissions

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.

Related research

People also read lists articles that other readers of this article have read.

Recommended articles lists articles that we recommend and is powered by our AI driven recommendation engine.

Cited by lists all citing articles based on Crossref citations.
Articles with the Crossref icon will open in a new tab.