A highly effective Pd/Cu-catalyzed coupling reaction of terminal alkynes with organic halides promoted by tetrabutylammonium fluoride or hydroxide

被引：0

作者：

Mori, A ^{[1
]}

Shimada, T ^{[1
]}

Kondo, T ^{[1
]}

Sekiguchi, A ^{[1
]}

机构：

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

来源：

SYNLETT | 2001年 / 05期

关键词：

Sonogashira-Hagihara coupling; Pd/Cu catalyst; terminal alkynes; tetrabutylammonium fluoride; tetrabutylammonium hydroxide; polycondensation;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Coupling reaction of terminal alkynes catalyzed by Pd/ Cu with several organic electrophiles is shown to proceed by use of tetrabutylammonium fluoride (TBAF) or tetrabutylammonium hydroxide(TBAOH) as an activator. Treatment of l-octyne and 4-methoxy-iodobenzene in the presence of 2.0 equiv of TBAOH, 1 mol% of PdCl2(PPh3)(3), and 2 mol% of Cul affords: 1-phenyl-1-octyne in 98% yield after stirring at room temperature for 1 h. The new coupling reaction is also applied to polymer synthesis via polycondensation of a diyne and a diiodoarene.

引用

页码：649 / 651

页数：3

共 50 条

[21] Multicomponent Reaction: Pd/Cu-Catalyzed Borocarbonylation of Aryldiazonium Salts with Aliphatic Terminal Alkynes to gem-Bis(boryl) Ketones
Zhu, Fengxiang
Yin, Pengpeng
CHEMISTRY-A EUROPEAN JOURNAL, 2023,
[22] Direct dehydrative cross-coupling of tautomerizable heterocycles with alkynes via Pd/Cu-catalyzed phosphonium coupling
Kang, Fu-An
Lanter, James C.
Cai, Chaozhong
Sui, Zhihua
Murray, William V.
CHEMICAL COMMUNICATIONS, 2010, 46 (08) : 1347 - 1349
[23] Synthesis of Unsymmetrical 1,3-Diynes via Pd/Cu-Catalyzed Cross-Coupling of Terminal Alkynes at Room Temperature
Liu, Yashuai
Liu, Ping
Gu, Ningning
Xie, Jianwei
Liu, Yan
Dai, Bin
CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (09) : 895 - 900
[24] Construction of Substituted Benzenes via Pd-Catalyzed Cross-Coupling/Cyclization Reaction of Vinyl Halides and Terminal Alkynes
Xie, Meihua
Wang, Shengke
Wang, Jun
Fang, Kuang
Liu, Changqing
Zha, Chao
Jia, Jing
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (08): : 3329 - 3334
[25] Cu(I)-catalyzed proline promoted one-pot reaction of aryl halides, NaN3 and terminal alkynes.
Feldman, AK
Colasson, B
Fokin, VV
Sharpless, KB
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U149 - U149
[26] CuI-catalyzed coupling reaction of aryl halides with terminal alkynes in the absence of palladium and phosphine
Ma, DW
Liu, F
CHEMICAL COMMUNICATIONS, 2004, (17) : 1934 - 1935
[27] Cu-catalyzed transannulation reaction of pyridotriazoles with terminal alkynes under aerobic conditions: efficient synthesis of indolizines
Helan, V.
Gulevich, A. V.
Gevorgyan, V.
CHEMICAL SCIENCE, 2015, 6 (03) : 1928 - 1931
[28] Cu-Catalyzed Cross-Coupling Reactions of Enamines and Terminal Alkynes: Access of Propargylamines as Neurodegenerative Disorder Agents
Mohan, Lakavathu
Lee, Ji Eun
Srinivasarao, Mande
Cutright, Alexander J.
Raju, Selvam
Stokes, Sean. L.
Emerson, Joseph. P.
Kim, Jae Hong
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 12 (10)
[29] Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF)
Suzuki, N
Yasaki, S
Yasuhara, A
Sakamoto, T
CHEMICAL & PHARMACEUTICAL BULLETIN, 2003, 51 (10) : 1170 - 1173
[30] CARBONYLATIVE COUPLING REACTION OF ORGANOFLUOROSILANES WITH ORGANIC HALIDES PROMOTED BY FLUORIDE-ION AND PALLADIUM CATALYST
HATANAKA, Y
FUKUSHIMA, S
HIYAMA, T
TETRAHEDRON, 1992, 48 (11) : 2113 - 2126

← 1 2 3 4 5 →