Synthesis of functionalized alkynes via palladium-catalyzed Sonogashira reactions

被引：12

作者：

Ibrahim, Mansur B. ^{[1
]}

El Ali, Bassam ^{[1
]}

Malik, Imran ^{[1
]}

Fettouhi, Mohammed ^{[1
]}

机构：

[1] King Fahd Univ Petr & Minerals, Dept Chem, Dhahran 31261, Saudi Arabia

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 05期

关键词：

Palladium-bis(oxazoline); Sonogashira coupling; Diiodobenzene; Alkyl alkynes; Dialkynes; CROSS-COUPLING REACTIONS; COPPER-FREE; ARYL BROMIDES; SUZUKI-MIYAURA; TERMINAL ALKYNES; EFFICIENT; HECK; CHLORIDES; COMPLEX; LIGAND;

D O I：

10.1016/j.tetlet.2015.12.086

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient protocol for the copper and phosphine free Sonogashira cross-coupling reactions of aryl iodides with terminal alkynes under aerobic conditions has been developed. Using 1 mol % of the palladium-bis(oxazoline) complex, Pd-BOX A, in the presence of KOH, and a CH3CN-H2O solvent system allowed for the cross -coupling reactions to proceed at room temperature or 60 degrees C. This new catalytic system was found to be highly active for the cross-coupling reaction of aryl diiodo substrates with unactivated alkyl alkynes to produce various symmetrical dialkynes, as well as for the cross -coupling of terminal dialkynes with aryl iodides to generate symmetrical disubstituted internal alkynes. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：554 / 558

页数：5

共 48 条

[1] Palladium complexes derived from N,N-bidentate NH-iminophosphorane ligands: synthesis and use as catalysts in the Sonogashira reaction [J].

Alajarin, Mateo ;

Lopez-Leonardo, Carmen ;

Llamas-Lorente, Pilar ;

Raja, Rosalia ;

Bautista, Delia ;

Orenes, Raul-Angel .

DALTON TRANSACTIONS, 2012, 41 (39) :12259-12269

[2] Gold catalyzed oxycyclizations of alkynols and alkyndiols [J].

Alcaide, Benito ;

Almendros, Pedro ;

Miguel Alonso, Jose .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (12) :4405-4416

[3] A phenyldithiocarbazate-functionalized polyvinyl chloride resin-supported Pd(II) complex as an effective catalyst for solvent- and copper-free Sonogashira reactions under aerobic conditions [J].

Bakherad, Mohammad ;

Keivanloo, Ali ;

Samangooei, Shahrzad ;

Omidian, Mina .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 740 :78-82

[4] Solvent-free Heck and copper-free Sonogashira cross-coupling reactions catalyzed by a polystyrene-anchored Pd(II) phenyldithiocarbazate complex [J].

Bakherad, Mohammad ;

Keivanloo, Ali ;

Samangooei, Shahrzad .

TETRAHEDRON LETTERS, 2012, 53 (43) :5773-5776

[5] Copper- and solvent-free Sonogashira coupling reactions of aryl halides with terminal alkynes catalyzed by 1-phenyl-1,2-propanedione-2-oxime thiosemi-carbazone-functionalized polystyrene resin supported Pd(II) complex under aerobic conditions [J].

Bakherad, Mohammad ;

Keivanloo, Ali ;

Bahramian, Bahram ;

Jajarmi, Saeedeh .

APPLIED CATALYSIS A-GENERAL, 2010, 390 (1-2) :135-140

[6] A re-evaluation of the photophysical properties of 1,4-bis(phenylethynyl)benzene: A model for poly(phenyleneethynylene) [J].

Beeby, A ;

Findlay, K ;

Low, PJ ;

Marder, TB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) :8280-8284

[7] Bis(pyrimidine)-based palladium catalysts: synthesis, X-ray structure and applications in Heck-, Suzuki-, Sonogashira-Hagihara couplings and amination reactions [J].

Buchmeiser, MR ;

Schareina, T ;

Kempe, R ;

Wurst, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 634 (01) :39-46

[8] Rhodium-Catalyzed Polymerization of Phenylacetylene and its Derivatives [J].

Casado, Miguel A. ;

Fazal, Atif ;

Oro, Luis A. .

ARABIAN JOURNAL FOR SCIENCE AND ENGINEERING, 2013, 38 (07) :1631-1646

[9]

Chih-chung T., 2011, CHEM LETT, V40, P955

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

Chinchilla, Rafael ;

Najera, Carmen .

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

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