Copper-catalyzed synthesis of vinyl sulfides

被引:265
作者
Bates, CG [1 ]
Saejueng, P [1 ]
Doherty, MQ [1 ]
Venkataraman, D [1 ]
机构
[1] Univ Massachusetts, Dept Chem, Amherst, MA 01003 USA
关键词
D O I
10.1021/ol0477935
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3)(2)]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.
引用
收藏
页码:5005 / 5008
页数:4
相关论文
共 44 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]   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
[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]  
Deng W, 2004, CHINESE J ORG CHEM, V24, P150