Highly stereoselective hydrocarbation of terminal alkynes via Pt-catalyzed hydrosilylation/Pd-catalyzed cross-coupling reactions

被引:122
作者
Denmark, SE [1 ]
Wang, ZG [1 ]
机构
[1] Univ Illinois, Dept Chem, Roger Adams Lab 245, Urbana, IL 61801 USA
关键词
D O I
10.1021/ol0156751
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The formal addition of an aryl-H or alkenyl-H bond across a terminal alkyne has been accomplished by the combination of platinum-catalyzed hydrosilylation followed by palladium-catalyzed cross-coupling, The use of the t-Bu3P-Pt(DVDS) catalyst in combination with tetramethyldisiloxane gave excellent regio- and stereoselectivity with a number of alkyne substrates, Subsequent, fluoride-promoted cross-coupling proceeded in high yield and stereospecificity for a variety of aryl halides.
引用
收藏
页码:1073 / 1076
页数:4
相关论文
共 48 条
[11]  
DENMARK SE, 2000, ORG LETT, V2, P61
[12]  
DENMARK SE, IN PRESS J ORGANOMET
[13]  
Diederich F., 1998, METAL CATALYZED CROS, DOI DOI 10.1002/9783527612222
[14]   Shortcut syntheses of naturally occurring 5-alkylresorcinols with DNA-cleaving properties [J].
Furstner, A ;
Seidel, G .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2332-2336
[15]  
HECK RF, 1985, PALLDIUM REAGENTS OR
[16]   Substituent effect of 3,3,3-trifluoropropyl group on organic silanols. Palladium-mediated Mizoroki-Heck type and cross-coupling reactions [J].
Hirabayashi, K ;
Kondo, T ;
Toriyama, F ;
Nishihara, Y ;
Mori, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2000, 73 (03) :749-750
[17]   A new transformation of silanols. Palladium-catalyzed cross-coupling with organic halides in the presence of silver(I) oxide [J].
Hirabayashi, K ;
Kawashima, J ;
Nishihara, Y ;
Mori, A ;
Hiyama, T .
ORGANIC LETTERS, 1999, 1 (02) :299-301
[18]   PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF ORGANOMETALLOIDS THROUGH ACTIVATION WITH FLUORIDE-ION [J].
HIYAMA, T ;
HATANAKA, Y .
PURE AND APPLIED CHEMISTRY, 1994, 66 (07) :1471-1478
[19]  
Hiyama T, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P421
[20]   ORGANIC-SYNTHESIS USING HALOBORATION REACTION .21. A SYNTHESIS OF PROSTAGLANDIN B-1 METHYL-ESTER BY THE STEPWISE CROSS-COUPLING REACTION USING (E)-(2-BROMOETHENYL)DIISOPROPOXYBORANE [J].
HYUGA, S ;
HARA, S ;
SUZUKI, A .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1992, 65 (08) :2303-2305