Highly satisfactory alkynylation of alkenyl halides via Pd-catalyzed cross-coupling with alkynylzincs and its critical comparison with the Sonogashira alkynylation

被引：86

作者：

Negishi, EI ^{[1
]}

Qian, MX ^{[1
]}

Zeng, FX ^{[1
]}

Anastasia, L ^{[1
]}

Babinski, D ^{[1
]}

机构：

[1] Purdue Univ, HC Brown & RB Wetherill Labs Chem, W Lafayette, IN 47907 USA

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol030010F

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The Pd-catalyzed alkynylation of various alkenyl halides and triflates with alkynylzincs proceeds well even with alkynyl derivatives containing electron-withdrawing groups. The reaction appears to be highly general. Noteworthy is that the corresponding Sonogashira reactions under various reported conditions are significantly less satisfactory in all cases performed in this study.

引用

页码：1597 / 1600

页数：4

共 45 条

[1] A convenient route to unsymmetrical conjugated diynes
Alami, M
Ferri, F
[J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2763 - 2766
[2] HIGHLY DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-TRIMETHYLSILYL-1-EN-3-YNES, (1E,3Z)-1-TRIMETHYLSILYL-1,3-DIENES AND (1E,3E)-1-TRIMETHYLSILYL-1,3-DIENES
ANDREINI, BP
CARPITA, A
ROSSI, R
[J]. TETRAHEDRON LETTERS, 1988, 29 (18) : 2239 - 2242
[3] DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-TRIMETHYLSILYL-3-EN-1-YNES BY PALLADIUM-CATALYZED CROSS-COUPLING REACTION BETWEEN TRIMETHYLSILYLETHYNYLZINC CHLORIDE AND STEREOISOMERIC MIXTURES OF 1-BROMO-1-ALKENES
ANDREINI, BP
CARPITA, A
ROSSI, R
[J]. TETRAHEDRON LETTERS, 1986, 27 (45) : 5533 - 5534
[4] Synthesis of stipiamide and a new multidrug resistance reversal agent, 6,7-dehydrostipiamide
Andrus, MB
Lepore, SD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (09) : 2327 - 2328
[5] Total synthesis of stipiamide and designed polyenes as new agents for the reversal of multidrug resistance
Andrus, MB
Lepore, SD
Turner, TM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) : 12159 - 12169
[6] A NOVEL METHOD FOR CARBON-CARBON BOND FORMATION - PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF PHENYL FLUOROALKANESULFONATES WITH ORGANOZINC REAGENTS
CHEN, QY
HE, YB
[J]. TETRAHEDRON LETTERS, 1987, 28 (21) : 2387 - 2388
[7] DANG HP, 1987, TETRAHEDRON LETT, P191
[8] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES
DIECK, HA
HECK, FR
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) : 259 - 263
[9] A new method for synthesis of methyl arylpropiolates by direct Heck coupling of aryl iodide and methyl propiolate in presence of K2CO3
Eckert, T
Ipaktschi, J
[J]. SYNTHETIC COMMUNICATIONS, 1998, 28 (02) : 327 - 335
[10] Furstner A, 1996, LIEBIGS ANN, P2107

← 1 2 3 4 5 →