Palladium-catalyzed cross-coupling of silanols, silanediols, and silanetriols promoted by silver(I) oxide

被引：168

作者：

Hirabayashi, E ^{[1
]}

Mori, A ^{[1
]}

Kawashima, J ^{[1
]}

Suguro, M ^{[1
]}

Nishihara, Y ^{[1
]}

Hiyama, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Chem Resources Lab, Yokohama, Kanagawa 2268503, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 17期

关键词：

D O I：

10.1021/jo000679p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Palladium-catalyzed cross-coupling of aryl- or alkenylsilanols, silanediols, and silanetriols with a variety of iodoarenes by the catalysis of palladium(0) and in the presence of silver(I) oxide furnished the coupling products in good to excellent yields. The reactions of silanediols or silanetriols under similar conditions proceeded much faster than those of silanols to afford the corresponding coupling products in excellent yields within shorter reaction periods (5-12 h). The measurement of the X-ras diffraction (XRD) pattern of the silver residue after the reaction revealed that silver(I) oxide was converted to silver(I) iodide.

引用

页码：5342 / 5349

页数：8

共 47 条

[1] PREPARATION OF ORGANOSILANOLS VIA METAL-CATALYZED REACTION OF ORGANOSILICON HYDRIDES WITH WATER
BARNES, GH
DAUGHENB.NE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1966, 31 (03) : 885 - &
[2] SYNTHESES OF NITROSUBSTITUTED CIS-BIS(PHENYL)PLATINUM(II) COMPOUNDS
BRUNE, HA
STAPP, B
SCHMIDTBERG, G
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1986, 307 (01) : 129 - 137
[3] THE PALLADIUM-CATALYZED REACTION OF ARYL IODIDES WITH MONOSUBSTITUTED AND DISUBSTITUTED ACETYLENES - A NEW SYNTHESIS OF TRISUBSTITUTED ALKENES
CACCHI, S
FELICI, M
PIETRONI, B
[J]. TETRAHEDRON LETTERS, 1984, 25 (29) : 3137 - 3140
[4] CHA TH, 1988, J CHEM SOC CHEM COMM, P1280
[5] ENANTIOSELECTIVE SYNTHESIS OF EPOXIDES VIA SHARPLESS EPOXIDATION OF ALKENYLSILANOLS
CHAN, TH
CHEN, LM
WANG, D
LI, LH
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1993, 71 (01): : 60 - 67
[6] DEMARK SE, 1999, Z ORG LETT, V1, P1495
[7] Highly stereospecific, palladium-catalyzed cross-coupling of alkenylsilanols
Denmark, SE
Wehrli, D
[J]. ORGANIC LETTERS, 2000, 2 (04) : 565 - 568
[8] Highly stereospecific, cross-coupling reactions of alkenylsilacyclobutanes
Denmark, SE
Choi, JY
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (24) : 5821 - 5822
[9] REACTIVITY OF ORGANOMAGNESIUM WITH ACETYLENIC-COMPOUNDS IN PRESENCE OF NICKEL-COMPLEX (PPH3)2NICL2
DUBOUDIN, JG
JOUSSEAUME, B
SAUX, A
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1978, 162 (02) : 209 - 222
[10] PALLADIUM-CATALYZED COUPLING OF ARYLSTANNANES WITH ORGANIC SULFONATES - A COMPREHENSIVE STUDY
FARINA, V
KRISHNAN, B
MARSHALL, DR
ROTH, GP
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (20) : 5434 - 5444

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