A general method for the formation of aryl-sulfur bonds using copper(I) catalysts

被引：422

作者：

Bates, CG ^{[1
]}

Gujadhur, RK ^{[1
]}

Venkataraman, D ^{[1
]}

机构：

[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol0264105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We report a mild, palladium-free synthetic protocol for the cross-coupling reaction of aryl iodides and thiols using 10 mol % Cul and 10 mol % neocuproine, with NaOt-Bu as the base, in toluene at 110 degreesC. Using this protocol, we have shown that a variety of aryl sulfides can be synthesized in excellent yields from readily available iodides and thiols.

引用

页码：2803 / 2806

页数：4

共 39 条

[1] Synthesis of thiols, selenols, sulfides, selenides, sulfoxides, selenoxides, sulfones and selenones
Baird, CP
Rayner, CM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (12): : 1973 - 2003
[2] CARBON-HETEROATOM BOND-FORMING REDUCTIVE ELIMINATION - MECHANISM, IMPORTANCE OF TRAPPING REAGENTS, AND UNUSUAL ELECTRONIC EFFECTS DURING FORMATION OF ARYL SULFIDES
BARANANO, D
HARTWIG, JF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (10) : 2937 - 2938
[3] A NEW, PALLADIUM-CATALYZED SYNTHESIS OF AROMATIC MERCAPTURIC ACID-DERIVATIVES
CIATTINI, PG
MORERA, E
ORTAR, G
[J]. TETRAHEDRON LETTERS, 1995, 36 (23) : 4133 - 4136
[4] Using intelligent/random library screening to design focused libraries for the optimization of homogeneous catalysts: Ullmann ether formation
Fagan, PJ
Hauptman, E
Shapiro, R
Casalnuovo, A
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (21) : 5043 - 5051
[5] Ligand-accelerated catalysis of the Ullmann condensation: Application to hole conducting triarylamines
Goodbrand, HB
Hu, NX
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) : 670 - 674
[6] Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst
Gujadhur, R
Venkataraman, D
[J]. SYNTHETIC COMMUNICATIONS, 2001, 31 (18) : 2865 - 2879
[7] Formation of aryl-nitrogen bonds using a soluble copper(I) catalyst
Gujadhur, R
Venkataraman, D
Kintigh, JT
[J]. TETRAHEDRON LETTERS, 2001, 42 (29) : 4791 - 4793
[8] Formation of aryl-nitrogen, aryl-oxygen, and aryl-carbon bonds using well-defined copper(I)-based catalysts
Gujadhur, RK
Bates, CG
Venkataraman, D
[J]. ORGANIC LETTERS, 2001, 3 (26) : 4315 - 4317
[9] Carbon-heteroatom bond-forming reductive eliminations of amines, ethers, and sulfides
Hartwig, JF
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (12) : 852 - 860
[10] A general and mild copper-catalyzed arylation of diethyl malonate
Hennessy, EJ
Buchwald, SL
[J]. ORGANIC LETTERS, 2002, 4 (02) : 269 - 272

← 1 2 3 4 →