Non-Sonogashira-type palladium-catalyzed coupling reactions of terminal alkynes assisted by silver(I) oxide or tetrabutylammonium fluoride

被引：148

作者：

Mori, A ^{[1
]}

Kawashima, J ^{[1
]}

Shimada, T ^{[1
]}

Suguro, M ^{[1
]}

Hirabayashi, K ^{[1
]}

Nishihara, Y ^{[1
]}

机构：

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

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 19期

关键词：

D O I：

10.1021/ol0061586

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Palladium-catalyzed reaction of aryl and alkenyl halides with terminal alkynes in the presence of silver(I) oxide as an activator furnishes various arylated or alkenylated alkynes in good to excellent yields, The similar coupling reaction is also found to proceed using tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide (TBAOH) as an activator.

引用

页码：2935 / 2937

页数：3

共 24 条

[11] A new transformation of silanols. Palladium-catalyzed cross-coupling with organic halides in the presence of silver(I) oxide
Hirabayashi, K
Kawashima, J
Nishihara, Y
Mori, A
Hiyama, T
[J]. ORGANIC LETTERS, 1999, 1 (02) : 299 - 301
[12] HIRABAYASHI K, IN PRESS J ORG CHEM
[13] Hiyama T, 1998, METAL-CATALYZED CROSS-COUPLING REACTIONS, P421
[14] HOSOMI A, 1978, TETRAHEDRON LETT, P3043
[15] Silver salt-promoted direct cross-coupling reactions of alkynylsilanes with aryl iodides: synthesis of aryl-substituted alkynylamides
Koseki, Y
Omino, K
Anzai, S
Nagasaka, T
[J]. TETRAHEDRON LETTERS, 2000, 41 (14) : 2377 - 2380
[16] Isolation of the transmetalation step in the Hiyama cross-coupling reaction of organosilanes
Mateo, C
FernandezRivas, C
Echavarren, AM
Cardenas, DJ
[J]. ORGANOMETALLICS, 1997, 16 (10) : 1997 - 1999
[17] Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes
Nishihara, Y
Ikegashira, K
Hirabayashi, K
Ando, J
Mori, A
Hiyama, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (06) : 1780 - 1787
[18] Cu(I)/Pd(0)-catalyzed cross-coupling reaction of alkynylsilanes with aryl or alkenyl triflates: "Sila"-Sonogashira-Hagihara coupling
Nishihara, Y
Ikegashira, K
Mori, A
Hiyama, T
[J]. CHEMISTRY LETTERS, 1997, (12) : 1233 - 1234
[19] A novel cross-coupling polycondensation of alkynylsilanes with aryl triflates catalyzed by CuCl/Pd(PPh3)4
Nishihara, Y
Ando, J
Kato, T
Mori, A
Hiyama, T
[J]. MACROMOLECULES, 2000, 33 (08) : 2779 - 2781
[20] Utilization of tetrabutylammonium triphenyldifluorosilicate as a fluoride source for silicon-carbon bond cleavage
Pilcher, AS
DeShong, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) : 6901 - 6905

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