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

[1] Ligand-free Pd/Cu-catalyzed decarboxylative coupling of aryl iodides with α-oxocarboxylates
Ji, Yongfeng
Yang, Xiaomin
Mao, Weixi
[J]. APPLIED ORGANOMETALLIC CHEMISTRY, 2014, 28 (09) : 678 - 680
[2] A highly efficient, ligand-free and recyclable SBA-15 supported Cu2O catalyzed cyanation of aryl iodides with potassium hexacyanoferrate(II)
Yin, Wenzhu
Liu, Rui
He, Guangke
Lv, Wangjie
Zhu, Hongjun
[J]. RSC ADVANCES, 2014, 4 (71): : 37773 - 37778
[3] Ligand-free copper-catalyzed C-S coupling of aryl iodides and thiols
Sperotto, Elena
van Klink, Gerard P. M.
de Vries, Johannes G.
van Koten, Gerard
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (14): : 5625 - 5628
[4] Ligand-free palladium catalyzed phosphorylation of aryl iodides
Nowrouzi, Najmeh
Keshtgar, Saba
Jahromi, Enayatollah Bahman
[J]. TETRAHEDRON LETTERS, 2016, 57 (03) : 348 - 350
[5] Efficient ligand-free nickel-catalyzed C-S cross-coupling of thiols with aryl iodides
Jammi, Suribabu
Barua, Priyanka
Rout, Laxmidhar
Saha, Prasenjit
Punnlyamurthy, Tharmalingam
[J]. TETRAHEDRON LETTERS, 2008, 49 (09) : 1484 - 1487
[6] A Highly Efficient CuCl2-Catalyzed C-S Coupling of Aryl Iodides with Tetraalkylthiuram Disulfides: Synthesis of Aryl Dithiocarbamates
Cao, Qiang
Peng, Han-Ying
Cheng, Yu
Dong, Zhi-Bing
[J]. SYNTHESIS-STUTTGART, 2018, 50 (07): : 1527 - 1534
[7] Ligand-Free Pd/Cu-Catalyzed Aminosulfonylation of Aryl Iodides for Direct Sulfonamide Syntheses
Zhu, Haibo
Shen, Yajing
Deng, Qinyue
Le, Zhang-Gao
Tu, Tao
[J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (11) : 1542 - 1545
[8] Ligand-free palladium-catalyzed decarboxylative coupling reactions of aryl iodides and alkynyl carboxylic acids
Pyo, Ayoung
Kim, Ji Dang
Choi, Hyun Chul
Lee, Sunwoo
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 724 : 271 - 274
[9] Ligand-Free CuI-Catalyzed Chemoselective S-Arylation of 2-Mercaptobenzimidazole with Aryl Iodides
Tan, Bryan Yong-Hao
Teo, Yong-Chua
[J]. SYNLETT, 2018, 29 (15) : 2056 - 2060
[10] A highly efficient and recyclable ligand-free protocol for the Suzuki coupling reaction of potassium aryltrifluoroborates in water
Liu, Leifang
Dong, Yan
Tang, Nana
[J]. GREEN CHEMISTRY, 2014, 16 (04) : 2185 - 2189

← 1 2 3 4 5 →