Stereo- and regiospecific Cu-catalyzed, cross-coupling reaction of vinyl iodides and thiols: A very mild and general route for the synthesis of vinyl sulfides

被引：65

作者：

Kabir, M. Hahiahan ^{[1
]}

Van Linn, Michael L. ^{[1
]}

Monte, Aaron ^{[2
]}

Cook, James M. ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem & Biochem, Milwaukee, WI 53201 USA

[2] Univ Wisconsin, Dept Chem, La Crosse, WI 54601 USA

来源：

ORGANIC LETTERS | 2008年 / 10卷 / 15期

关键词：

D O I：

10.1021/ol801149n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A mild and efficient method for the copper-catalyzed formation of vinylic carbon-sulfur bonds has been developed. The desired vinyl sulfides are obtained in good to excellent yields, with full retention of stereochemistry. This method is particularly noteworthy given its mild reaction conditions, simplicity, and generality, as well as low cost of the catalyst system.

引用

页码：3363 / 3366

页数：4

共 43 条

[1] Wittig approach to carbohydrate-derived vinyl sulfides, new substrates for regiocontrolled ring-closure reactions [J].

Aucagne, V ;

Tatibouët, A ;

Rollin, P .

TETRAHEDRON, 2004, 60 (08) :1817-1826

[2]

BACKVALL JE, 1994, J ORG CHEM, V59, P5850

[3] Copper-catalyzed synthesis of vinyl sulfides [J].

Bates, CG ;

Saejueng, P ;

Doherty, MQ ;

Venkataraman, D .

ORGANIC LETTERS, 2004, 6 (26) :5005-5008

[4] Studies of triphenylsilanethiol addition to alkynes: Preparation of vinyl sulfides [J].

Beauchemin, A ;

Gareau, Y .

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1998, 139 :187-192

[5] A USEFUL METHOD FOR CONFIGURATIONAL ASSIGNMENT OF VINYL SULFIDES - STEREOCHEMICAL REASSESSMENT OF THE RADICAL-ADDITION OF BENZENETHIOL TO ALKYNES [J].

BENATI, L ;

CAPELLA, L ;

MONTEVECCHI, PC ;

SPAGNOLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (08) :1035-1038

[6] FREE-RADICAL REACTIONS OF BENZENETHIOL AND DIPHENYL DISULFIDE WITH ALKYNES - CHEMICAL-REACTIVITY OF INTERMEDIATE 2-(PHENYLTHIO)VINYL RADICALS [J].

BENATI, L ;

MONTEVECCHI, PC ;

SPAGNOLO, P .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (09) :2103-2109

[7] PALLADIUM - CATALYZED-REACTIONS OF TRIALKYLSTANNYL PHENYL SULFIDES WITH ALKENYL BROMIDES - A NEW DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-ALKENYL PHENYL SULFIDES [J].

CARPITA, A ;

ROSSI, R ;

SCAMUZZI, B .

TETRAHEDRON LETTERS, 1989, 30 (20) :2699-2702

[8] Vinyl sulfide derivatives of truncated oxidosqualene as selective inhibitors of oxidosqualene and squalene-hopene cyclases [J].

Ceruti, M ;

Balliano, G ;

Rocco, F ;

Milla, P ;

Arpicco, S ;

Cattel, L ;

Viola, F .

LIPIDS, 2001, 36 (06) :629-636

[9] SYNTHESIS OF VINYL SELENIDES OR SULFIDES AND KETENE SELENOACETALS OR THIOACETALS BY NICKEL(II) VINYLATION OF SODIUM BENZENESELENOLATE OR BENZENETHIOLATE [J].

CRISTAU, HJ ;

CHABAUD, B ;

LABAUDINIERE, R ;

CHRISTOL, H .

JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (06) :875-878

[10] CuI-catalyzed coupling reactions of aryl iodides and bromides with thiols promoted by amino acid ligands [J].

Deng, W ;

Zou, Y ;

Wang, YF ;

Liu, L ;

Guo, QX .

SYNLETT, 2004, (07) :1254-1258

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