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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 12
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Original Articles

Cu(OAc)2-Catalyzed N-Arylation of Sulfonamides with Arylboronic Acids or Trimethoxy(phenyl)silane

Changduo Pan College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
,
Jiang Cheng College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
,
Huayue Wu College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
,
Jinchang Ding College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, China
&
Miaochang Liu College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou, ChinaCorrespondence[email protected]
Pages 2082-2092 | Received 07 May 2008, Published online: 13 May 2009

Citations (28)

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Zijian Zhao, Yan Lian, Chang Zhao & Bing Wang. (2018) Palladium-catalyzed desulfitative arylation of sulfonamides with sodium arylsulfinates. Synthetic Communications 48:12, pages 1436-1442.
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Articles from other publishers (27)

Karolína Salvadori, Michal Churý, Jan Budka, Jakub Harvalík, Pavel Matějka, Ludmila Šimková & Pavel Lhoták. (2024) Chemoselective Electrochemical Cleavage of Sulfonimides as a Direct Way to Sulfonamides. The Journal of Organic Chemistry 89:3, pages 1425-1437.
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Lachlan J. N. Waddell, Martyn C. Henry, Mohamed A. B. Mostafa & Andrew Sutherland. (2022) One-Pot Synthesis of Diaryl Sulfonamides using an Iron- and Copper-Catalyzed Aryl C–H Amidation Process. Synthesis 54:20, pages 4551-4560.
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Haiying Tian, Ruiyan Li, Fang Guo & Xiuling Chen. (2022) An Efficient Method for the Preparation of Sulfonamides from Sodium Sulfinates and Amines. ChemistryOpen 11:8.
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Mahmoud Nasrollahzadeh, Zahra Nezafat, Khatereh Pakzad & Fatemeh Ahmadpoor. (2021) Synthesis of magnetic chitosan supported metformin-Cu(II) complex as a recyclable catalyst for N-arylation of primary sulfonamides. Journal of Organometallic Chemistry 948, pages 121915.
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Yasin Orooji, Khatereh Pakzad, Mahmoud Nasrollahzadeh & Mahmood Tajbakhsh. (2021) Novel magnetic lignosulfonate-supported Pd complex as an efficient nanocatalyst for N-arylation of 4-methylbenzenesulfonamide. International Journal of Biological Macromolecules 182, pages 564-573.
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Akram Ashouri, Saadi Samadi, Behzad Nasiri, Hossein Zamani & Somayeh Pourian. (2020) Development of a CuCl/phosphine system to catalyze phenylation and methylation of -tosyl aldimines with phenylboronic and methylboronic acids . Comptes Rendus. Chimie 23:9-10, pages 575-581.
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Xiaolan Jiang, Kaili Zhang, Rongrong Zhao, Die Bai, Jinlong Wang, Binbin Li, Qixing Liu & Haifeng Zhou. (2020) Metal-free one-pot synthesis of N-arylsulfonamides from nitroarenes and sodium sulfinates in an aqueous medium. Tetrahedron Letters 61:42, pages 152397.
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Kaili Zhang, Yin Zhang, Qixing Liu, Dan He, Juyan Tian & Haifeng Zhou. (2019) Metal‐Free One‐Pot Synthesis of Sulfonamides from Nitroarenes and Arylsulfonyl Chlorides in Water. ChemistrySelect 4:25, pages 7413-7415.
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Wanrong Dong, Chaoyang Liu, Xinchi Ma, Yingjun Zhang, Zhihong Peng, Dexun Xie & Delie An. (2019) Copper-catalyzed denitrogenative N-arylation of sulfoximines and sulfonamides with arylhydrazines. Tetrahedron 75:29, pages 3886-3893.
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Banafsheh Mokhtari, Davood Nematollahi & Hamid Salehzadeh. (2019) A tunable pair electrochemical strategy for the synthesis of new benzenesulfonamide derivatives. Scientific Reports 9:1.
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Bo Yang, Chang Lian, Guanglu Yue, Danyang Liu, Liyan Wei, Yi Ding, Xiancai Zheng, Kui Lu, Di Qiu & Xia Zhao. (2018) Synthesis of N -arylsulfonamides through a Pd-catalyzed reduction coupling reaction of nitroarenes with sodium arylsulfinates . Organic & Biomolecular Chemistry 16:43, pages 8150-8154.
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Banlai Ouyang, Yanxia Zheng, Yi Liu, Fei Liu, Juying Yao & Yiyuan Peng. (2018) Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides. Tetrahedron Letters 59:41, pages 3694-3698.
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Jun Jiang, Sheng Zeng, De Chen, Chaozhihui Cheng, Wei Deng & Jiannan Xiang. (2018) Synthesis of N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium . Organic & Biomolecular Chemistry 16:27, pages 5016-5020.
Crossref
Banafsheh Mokhtari, Davood Nematollahi & Hamid Salehzadeh. (2018) Paired electrochemical conversion of nitroarenes to sulfonamides, diarylsulfones and bis(arylsulfonyl)aminophenols. Green Chemistry 20:7, pages 1499-1505.
Crossref
Tomas Javorskis & Edvinas Orentas. (2017) Chemoselective Deprotection of Sulfonamides Under Acidic Conditions: Scope, Sulfonyl Group Migration, and Synthetic Applications. The Journal of Organic Chemistry 82:24, pages 13423-13439.
Crossref
Dineshwori Chanu Loukrakpam & Prodeep Phukan. (2017) CuI catalyzed sulfamidation of arylboronic acid using TsNBr2 at room temperature. Tetrahedron Letters 58:52, pages 4855-4858.
Crossref
Yangji Jiang, Yaping You, Wanrong Dong, Zhihong Peng, Yingjun Zhang & Delie An. (2017) Copper-Promoted Desulfitative N -Arylation of Sulfonamides and Sulfoximines with Sodium Arylsulfinates . The Journal of Organic Chemistry 82:11, pages 5810-5818.
Crossref
Feng Zhao, Bin Li, Huawen Huang & Guo-Jun Deng. (2016) Palladium-catalyzed N -arylsulfonamide formation from arylsulfonyl hydrazides and nitroarenes . RSC Advances 6:16, pages 13010-13013.
Crossref
Chongren You, Fang Yao, Tao Yan & Mingzhong Cai. (2016) A highly efficient heterogeneous copper-catalyzed Chan–Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides. RSC Advances 6:49, pages 43605-43612.
Crossref
Weixi Zhang, Junyao Xie, Bin Rao & Meiming Luo. (2015) Iron-Catalyzed N -Arylsulfonamide Formation through Directly Using Nitroarenes as Nitrogen Sources . The Journal of Organic Chemistry 80:7, pages 3504-3511.
Crossref
Mahmoud Nasrollahzadeh, Akbar Rostami-Vartooni, Ali Ehsani & Majid Moghadam. (2014) Fabrication, characterization and application of nanopolymer supported copper (II) complex as an effective and reusable catalyst for the CN bond cross-coupling reaction of sulfonamides with arylboronic acids in water under aerobic conditions. Journal of Molecular Catalysis A: Chemical 387, pages 123-129.
Crossref
Xiangxiang Cao, Yang Bai, Yanjun Xie & Guo-Jun Deng. (2014) Palladium-catalyzed arylation of aryl sulfonamides with cyclohexanones. Journal of Molecular Catalysis A: Chemical 383-384, pages 94-100.
Crossref
Soo-Yeon Moon, Jungsoo Nam, Kris Rathwell & Won-Suk Kim. (2014) Copper-Catalyzed Chan–Lam Coupling between Sulfonyl Azides and Boronic Acids at Room Temperature. Organic Letters 16:2, pages 338-341.
Crossref
Yong‐Chua Teo, Fui‐Fong Yong, Idzham Khalid Ithnin, Siew‐Hui Trionna Yio & Zhiyin Lin. (2012) Efficient Manganese/Copper Bimetallic Catalyst for N ‐Arylation of Amides and Sulfonamides Under Mild Conditions in Water . European Journal of Organic Chemistry 2013:3, pages 515-524.
Crossref
Jennifer X. Qiao & Patrick Y. S. Lam. 2011. Boronic Acids. Boronic Acids 315 361 .
Brandon R. Rosen, J. Craig Ruble, Thomas J. Beauchamp & Antonio Navarro. (2011) Mild Pd-Catalyzed N -Arylation of Methanesulfonamide and Related Nucleophiles: Avoiding Potentially Genotoxic Reagents and Byproducts . Organic Letters 13:10, pages 2564-2567.
Crossref
Changduo Pan, Jiang Cheng, Huayue Wu, Jinchang Ding & Miaochang Liu. (2009) ChemInform Abstract: Cu(OAc) 2 ‐Catalyzed N‐Arylation of Sulfonamides with Arylboronic Acids or Trimethoxy(phenyl)silane. . ChemInform 40:43.
Crossref

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