Microwave-Assisted Copper-Catalyzed Cross-Coupling Reaction of Thiols with Aryl Iodides in Water

被引：25

作者：

Chen, Yi-An ^{[1
]}

Badsara, Satpal Singh ^{[1
]}

Tsai, Wan-Ting ^{[1
]}

Lee, Chin-Fa ^{[1
]}

机构：

[1] Natl Chung Hsing Univ, Dept Chem, Taichung 402, Taiwan

来源：

SYNTHESIS-STUTTGART | 2015年 / 47卷 / 02期

关键词：

microwave heating; copper; cross-coupling; thiols; aryl iodides; sulfides; S BOND FORMATION; C-H FUNCTIONALIZATION; LIGAND-FREE; EFFICIENT SYNTHESIS; METAL-FREE; ORGANIC-SYNTHESIS; TE BOND; HALIDES; SULFUR; CONVENIENT;

D O I：

10.1055/s-0034-1379206

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave-promoted C-S bond formation from thiols and aryl iodides in the presence of a copper catalyst is reported. A combination of copper(II) oxide and 1,10-phenanthroline catalyzes this reaction. A variety of aryl iodides react smoothly with thiols to provide the corresponding aryl sulfides in good to excellent yields. Notably, the reactions proceed in water with a short reaction time (30 minutes). This system shows broad functional-group tolerance; amino, chloro, bromo, acetyl, and nitro groups are unaffected by the reaction conditions.

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页码：181 / 186

页数：6

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共 90 条

[1] COBALT(II) CHLORIDE CATALYZED COUPLING OF THIOLS AND ANHYDRIDES - A NEW AND EFFICIENT SYNTHESIS OF THIOL ESTERS [J].

AHMAD, S ;

IQBAL, J .

TETRAHEDRON LETTERS, 1986, 27 (32) :3791-3794

[2] Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent [J].

Ajiki, K ;

Hirano, M ;

Tanaka, K .

ORGANIC LETTERS, 2005, 7 (19) :4193-4195

[3] Recent developments in microwave-assisted, transition-metal-catalysed C-C and C-N bond-forming reactions [J].

Appukkuttan, Prasad ;

Van der Eycken, Erik .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (07) :1133-1155

[4] Metal-free sp3 C-H functionalization: a novel approach for the syntheses of selenide ethers and thioesters from methyl arenes [J].

Badsara, Satpal Singh ;

Liu, Yi-Chen ;

Hsieh, Ping-An ;

Zeng, Jing-Wen ;

Lu, Shao-Yi ;

Liu, Yi-Wei ;

Lee, Chin-Fa .

CHEMICAL COMMUNICATIONS, 2014, 50 (77) :11374-11377

[5] Microwave-Assisted Ullmann C-S Bond Formation: Synthesis of the P38α MAPK Clinical Candidate VX-745 [J].

Bagley, Mark C. ;

Davis, Terence ;

Dix, Matthew C. ;

Fusillo, Vincenzo ;

Pigeaux, Morgane ;

Rokicki, Michal J. ;

Kipling, David .

JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (21) :8336-8342

[6] Rapid Ullmann-type synthesis of aryl sulfides using a copper(I) catalyst and ligand under microwave irradiation [J].

Bagley, Mark C. ;

Dix, Matthew C. ;

Fusillo, Vincenzo .

TETRAHEDRON LETTERS, 2009, 50 (26) :3661-3664

[7] Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites [J].

Baig, R. B. Nasir ;

Varma, Rajender S. .

GREEN CHEMISTRY, 2013, 15 (02) :398-417

[8] Carbon-Sulfur Bond Formation Catalyzed by [Pd(IPr*OMe)(cin)Cl] (cin = cinnamyl) [J].

Bastug, Gulluzar ;

Nolan, Steven P. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18) :9303-9308

[9] A general method for the formation of aryl-sulfur bonds using copper(I) catalysts [J].

Bates, CG ;

Gujadhur, RK ;

Venkataraman, D .

ORGANIC LETTERS, 2002, 4 (16) :2803-2806

[10] Unusual influence of the structures of transition metal complexes on catalytic C-S and C-Se bond formation under homogeneous and heterogeneous conditions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) :3431-3444

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