Copper-Catalyzed Sonogashira Reaction in Water

被引：31

作者：

Liu, Yujia ^{[1
]}

Blanchard, Vincent ^{[1
]}

Danoun, Gregory ^{[1
]}

Zhang, Zhaoyang ^{[2
]}

Tlili, Anis ^{[1
]}

Zhang, Wenlong ^{[2
]}

Monnier, Florian ^{[1
]}

Van der Lee, Arie ^{[3
]}

Mao, Jincheng ^{[2
]}

Taillefer, Marc ^{[1
]}

机构：

[1] Inst Charles Gerhardt, CNRS, Ecole Natl Super Chim Montpellier, UMR 5253, 8 Rue Ecole Normale, F-34296 Montpellier 05, France

[2] Southwest Petr Univ, State Key Lab Oil & Gas Reservoir Geol & Exploita, Chengdu 610500, Sichuan, Peoples R China

[3] Univ Montpellier, CNRS, Inst Europeen Membranes, ENSCM,UMR 5635, F-34095 Montpellier 5, France

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 35期

关键词：

copper-catalyzed; mechanism; Sonogashira; turn-over; water; PALLADIUM-FREE CONDITIONS; ARYL IODIDES; COUPLING REACTIONS; TERMINAL ALKYNES; CONJUGATED ENYNES; BOND FORMATION; VINYL IODIDES; ARYLATION; EFFICIENT; LIGANDS;

D O I：

10.1002/slct.201702854

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Copper-catalyzed Sonogashira reaction has been realized under biphasic conditions (water / organic substrates) allowing decreasing the copper loading up to 0.02-0.2 mol %. A potential intermediate species of the reaction, corresponding to a copper cluster linked with acetylide moiety, has been identified.

引用

页码：11599 / 11602

页数：4

共 37 条

[1] Structural systematics of some trinuclear alkynyl and diynyl Group 11 complexes containing dppm [dppm = CH2(PPh2)2] [J].

Bruce, Michael I. ;

Halet, Jean-Francois ;

Le Guennic, Boris ;

Skelton, Brian W. ;

Sobolev, Alexandre N. ;

Sumby, Christopher J. ;

White, Allan H. .

COORDINATION CHEMISTRY REVIEWS, 2018, 375 :2-12

[2] CuI/PPh3/PEG-WATER: AN EFFICIENT CATALYTIC SYSTEM FOR CROSS-COUPLING REACTION OF ARYL IODIDES AND ALKYNES [J].

Chen, Gong ;

Xie, Jianwei ;

Weng, Jiang ;

Zhu, Xinhai ;

Zheng, Zhanchao ;

Cai, Jiwen ;

Wan, Yiqian .

SYNTHETIC COMMUNICATIONS, 2011, 41 (21) :3123-3133

[3] The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL REVIEWS, 2007, 107 (03) :874-922

[4] Recent advances in Sonogashira reactions [J].

Chinchilla, Rafael ;

Najera, Carmen .

CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121

[5] Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides [J].

Cristau, HJ ;

Cellier, PP ;

Spindler, JF ;

Taillefer, M .

CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (22) :5607-5622

[6] Direct Copper-Catalyzed α-Arylation of Benzyl Phenyl Ketones with Aryl Iodides: Route towards Tamoxifen [J].

Danoun, Gregory ;

Tlili, Anis ;

Monnier, Florian ;

Taillefer, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (51) :12815-12819

[7] Palladium-based catalytic systems for the synthesis of conjugated enynes by Sonogashira reactions and related alkynylations [J].

Doucet, Henri ;

Hierso, Jean-Cyrille .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (06) :834-871

[8]

Glaser C., 1869, Chem. Ber, V2, P422, DOI 10.1002/cber.186900201183

[9] CuI/PPh3 catalyzed Sonogashira coupling reaction of aryl iodides with terminal alkynes in water in the absence of palladium [J].

Guan, Jin Tao ;

Yu, Guang-Ao ;

Chen, Lei ;

Weng, Tan Qing ;

Yuan, Jing Jing ;

Liu, Sheng Hua .

APPLIED ORGANOMETALLIC CHEMISTRY, 2009, 23 (02) :75-77

[10]

Gudajhur R. K., 2001, ORG LETT, V3, P4315

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