Dimethylaminoalkyl chalcogenolate palladium(II) complexes as an efficient copper- and phosphine-free catalyst for Sonogashira reaction

被引：18

作者：

Khairnar, Bhikan J. ^{[1
]}

Dey, Sandip ^{[2
]}

Jam, Vimal K. ^{[2
]}

Bhanage, Bhalchandra M. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Chem, Bombay 400019, Maharashtra, India

[2] Bhabha Atom Res Ctr, Div Chem, Bombay 400085, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 03期

关键词：

Sonogashira reaction; Chalcogenolate; Palladium complex; Phosphine free; Copper free; CARBON COUPLING REACTIONS; TERMINAL ALKYNES; LIGAND; ACID;

D O I：

10.1016/j.tetlet.2013.12.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N,N-Dimethylaminoalkyl chalcogenolate Pd(II) complexes [PdCI((ENMe2)-N-boolean AND)](n) has been investigated as a moisture/air-stable and robust catalyst for Sonogashira cross-coupling reaction in the absence of copper and phosphine ligand. The dimeric palladium(II) complex of selenium containing ligand shows the best catalytic activity as compared with monomeric and trimeric complexes. The variety of functional groups are tolerated under optimized catalytic systems and provide excellent yields of the products. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：716 / 719

页数：4

共 32 条

[1] Metal- and ligand-accelerated catalysis of the Baylis-Hillman reaction [J].

Aggarwal, VK ;

Mereu, A ;

Tarver, GJ ;

McCague, R .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7183-7189

[2] A copper- and amine-free Sonogashira coupling reaction promoted by a ferrocene-based phosphinimine-phosphine ligand at low catalyst loading [J].

Arques, A ;

Auñon, D ;

Molina, P .

TETRAHEDRON LETTERS, 2004, 45 (22) :4337-4340

[3] Isolation of an [SNS]Pd(II) pincer with a water ladder and its Suzuki coupling activity in water [J].

Bai, Shi-Qiang ;

Hor, T. S. Andy .

CHEMICAL COMMUNICATIONS, 2008, (27) :3172-3174

[4] Selenoether ligand assisted Heck catalysis [J].

Chakraborty, Tapash ;

Srivastava, Kriti ;

Singh, Harkesh B. ;

Butcher, Ray J. .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2011, 696 (13) :2559-2564

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

Chinchilla, Rafael ;

Najera, Carmen .

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

[6] A simple and efficient copper-free catalytic system based on a palladacycle for the arylation of alkynes [J].

Consorti, CS ;

Flores, FR ;

Rominger, F ;

Dupont, J .

ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (1-2) :133-141

[7] Tetradentate selenium ligand as a building block for homodinuclear complexes of Pd(II) and Ru(II) having seven membered rings or bis- pincer coordination mode: high catalytic activity of Pd-complexes for Heck reaction [J].

Das, Dipanwita ;

Singh, Pradhumn ;

Singh, Monika ;

Singh, Ajai Kumar .

DALTON TRANSACTIONS, 2010, 39 (45) :10876-10882

[8] 3-dimethylammopropyl chalcogenolate complexes of palladium(II):: Syntheses and characterization, including the crystal structures of [Pd(OAc)(ECH2CH2CH2NMe2)]2 • H2O(E = S, Se) and [PdCl(TeCH2CH2CH2NMe2)]2 [J].

Dey, S ;

Jain, VK ;

Varghese, B ;

Schurr, T ;

Niemeyer, M ;

Kaim, W ;

Butcher, RJ .

INORGANICA CHIMICA ACTA, 2006, 359 (05) :1449-1457

[9] 2-(Dimethylamino)ethaneselenolates of palladium(II): synthesis, structure, spectroscopy and transformation into palladium selenide [J].

Dey, S ;

Jain, VK ;

Chaudhury, S ;

Knoedler, A ;

Lissner, F ;

Kaim, W .

JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (05) :723-728

[10] 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

← 1 2 3 4 →