A Highly Efficient, Ligand-Free, and Recyclable Cu2S-Catalyzed Coupling of Aryl Iodides with Diaryl Disulfides

被引：75

作者：

Wang, Huifeng ^{[1
]}

Jiang, Linlin ^{[1
]}

Chen, Tao ^{[1
]}

Li, Yaming ^{[1
]}

机构：

[1] Dalian Univ Technol, State Key Lab Fine Chem, Dalian 116012, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 12期

基金：

中国国家自然科学基金;

关键词：

Copper; Cross-coupling; Sulfur; Sustainable chemistry; Heterogeneous catalysis; COPPER-CATALYZED SYNTHESIS; S BOND FORMATION; C-N; DIPHENYL DISELENIDE; ORGANOBORONIC ACIDS; ARYLBORONIC ACIDS; NICKEL-CATALYST; THIOLS; HALIDES; ARYLATION;

D O I：

10.1002/ejoc.201000003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient and ligand-free copper(I) sulfide catalyzed cross-coupling reaction of aryl iodides with diaryl disulfides was developed. With only 1 mol-% of Cu2S as the catalyst, iron powder as the reductant, and K2CO3 as the base, aryl iodides reacted with disulfides in DMSO at 90-110 degrees C for 18 24 h under an atmosphere of argon to give the corresponding aryl sulfides in good to excellent yields. In addition, the catalyst is recyclable and reusable with some loss of activity.

引用

页码：2324 / 2329

页数：6

共 50 条

[21] Efficient ligand-free copper-catalyzed C-S cross-coupling of thiols with aryl iodides using KF/Al2O3 as base
Feng, Yi-Si
Li, Yuan-Yuan
Tang, Lin
Wu, Wei
Xu, Hua-Jian
[J]. TETRAHEDRON LETTERS, 2010, 51 (18) : 2489 - 2492
[22] Substrate-promoted ligand-free CuI catalyzed S-arylation of 2-mercaptobenzothiazoles with aryl iodides in water
He, Guozhen
Huang, Yuan
Tong, Yao
Zhang, Jie
Zhao, Dan
Zhou, Shuangli
Han, Shiqing
[J]. TETRAHEDRON LETTERS, 2013, 54 (39) : 5318 - 5321
[23] Recyclable heterogeneous copper oxide on alumina catalyzed coupling of phenols and alcohols with aryl halides under ligand-free conditions
Swapna, Kokkirala
Murthy, Sabbavarapu Narayana
Jyothi, Mocharla Tarani
Nageswar, Yadavalli Venkata Durga
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (17) : 5978 - 5988
[24] Ligand-free Palladium/Copper Co-catalyzed Direct Arylation of Polyfluoroarenes with Aryl Iodides
Zhang, Xinyan
Yu, Jian
Yan, Guobing
[J]. ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 2013, 68 (08): : 885 - 890
[25] Synthesis of aryl-substituted indanones and indenes via a highly efficient ligand-free palladium-catalyzed Suzuki coupling process
Song, Yuming
Xie, Yamei
Chen, Minjian
Qu, Jingping
Hu, Hongfan
Lang, Xiaomei
Xue, Shan
Ran, Yin
Xin, Shixuan
[J]. ARKIVOC, 2016, : 306 - 327
[26] Ligand-Free Copper-Catalyzed Synthesis of Diaryl Thioethers from Aryl Halides and Thioacetamide
Tao, Chuanzhou
Lv, Aifeng
Zhao, Nan
Yang, Shuai
Liu, Xiaolang
Zhou, Jian
Liu, Weiwei
Zhao, Jing
[J]. SYNLETT, 2011, (01) : 134 - 138
[27] Nickel-Catalyzed Ligand-Free Hiyama Coupling of Aryl Bromides and Vinyltrimethoxysilane
Wei, Shichao
Mao, Yongjun
Shi, Shi-Liang
[J]. SYNLETT, 2021, 32 (16) : 1670 - 1674
[28] Solvent free, palladium catalyzed highly facile synthesis of diaryl disulfides from aryl thiols
Dutta, Pratip Kumar
Majumder, Arpi
Dutta, Sanjay
Dhar, Basab Bijayi
Munshi, Parthapratim
Sen, Subhabrata
[J]. TETRAHEDRON LETTERS, 2017, 58 (06) : 527 - 530
[29] Palladium-Catalyzed Ligand-Free Decarboxylative Coupling of α-Oxocarboxylic Acid with Aryl Diazonium Tetrafluoroborate: An Access to Unsymmetrical Diaryl Ketones
Panja, Subir
Maity, Pintu
Ranu, Brindaban C.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (20): : 12609 - 12618
[30] A Ligand-Free Palladium-Catalyzed Cross-Coupling of Aryl Sulfinates with Aryl Bromides
Ortgies, Dirk H.
Forgione, Pat
[J]. SYNLETT, 2013, 24 (13) : 1715 - 1721

← 1 2 3 4 5 →