Mixed phosphine/N-heterocyclic carbene-palladium complexes: synthesis, characterization, crystal structure and application in the Sonogashira reaction in aqueous media

被引：23

作者：

Aktas, Aydin ^{[1
]}

Erdemir, Fatos ^{[1
]}

Celepci, Duygu Barut ^{[2
]}

Gok, Yetkin ^{[1
]}

Aygun, Muhittin ^{[2
]}

机构：

[1] Inonu Univ, Dept Chem, Fac Sci, TR-44280 Malatya, Turkey

[2] Dokuz Eylul Univ, Dept Phys, Fac Sci, TR-35160 Izmir, Turkey

来源：

TRANSITION METAL CHEMISTRY | 2019年 / 44卷 / 03期

关键词：

COUPLING REACTION; SUZUKI-MIYAURA; ARYL CHLORIDES; COPPER FREE; LIGANDS; CATALYSTS; EFFICIENT;

D O I：

10.1007/s11243-018-0286-5

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of 2-hydroxyethyl-substituted N-heterocyclic carbene-(NHC)PdX2PPh3 complexes have been synthesized by substitution of the pyridine or 3-chloropyridine ligand in (NHC)PdX2(pyridine/3-chloropyridine) complexes with triphenylphosphine. The new complexes were characterized by H-1, C-13 {H-1}, P-31 {H-1}NMR, FTIR spectroscopy and elemental analysis. Also, the molecular and crystal structures of 1c and 1d have been obtained by single-crystal X-ray diffraction. The 2-hydroxyethyl-substituted (NHC)PdX2PPh3 complexes have been examined as catalysts for the Sonogashira cross-coupling reaction in water/DMF solvent mixtures.

引用

页码：229 / 236

页数：8

共 27 条

[1] 2-Hydroxyethyl-Substituted Pd-PEPPSI Complexes: Synthesis, Characterization and the Catalytic Activity in the Suzuki-Miyaura Reaction for Aryl Chlorides in Aqueous Media [J].

Aktas, Aydin ;

Celepci, Duygu Barut ;

Gok, Yetkin ;

Aygun, Muhittin .

CHEMISTRYSELECT, 2018, 3 (35) :9974-9980

[2] 2-Hydroxyethyl-Substituted (NHC)Pd(II)PPh3 Complexes: Synthesis, Characterization, Crystal Structure and Its Application on Sonogashira Cross-Coupling Reactions in Aqueous Media [J].

Aktas, Aydin ;

Celepci, Duygu Barut ;

Gok, Yetkin ;

Aygun, Muhittin .

CHEMISTRYSELECT, 2018, 3 (39) :10932-10937

[3] A STABLE CRYSTALLINE CARBENE [J].

ARDUENGO, AJ ;

HARLOW, RL ;

KLINE, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (01) :361-363

[4] Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].

Arpad Molnar .

CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320

[5] Synthesis and catalytic applications of palladium N-heterocyclic carbene complexes as efficient pre-catalysts for Suzuki-Miyaura and Sonogashira coupling reactions [J].

Boubakri, L. ;

Yasar, S. ;

Dorcet, V. ;

Roisnel, T. ;

Bruneau, C. ;

Hamdi, N. ;

Ozdemir, I. .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (12) :5105-5113

[6]

Caló V, 2000, EUR J ORG CHEM, V2000, P869

[7] Sonogashira cross-coupling reaction catalyzed by N-heterocyclic carbene-Pd(II)-PPh3 complexes under copper free and aerobic conditions [J].

Dehimat, Zineb Imene ;

Yasar, Sedat ;

Tebbani, Dahmane ;

Ozdemir, Ismail .

INORGANICA CHIMICA ACTA, 2018, 469 :325-334

[8] OLEX2: a complete structure solution, refinement and analysis program [J].

Dolomanov, Oleg V. ;

Bourhis, Luc J. ;

Gildea, Richard J. ;

Howard, Judith A. K. ;

Puschmann, Horst .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2009, 42 :339-341

[9] NHC-Ru complexes- Friendly catalytic tools for manifold chemical transformations [J].

Dragutan, Valerian ;

Dragutan, Ileana ;

Delaude, Lionel ;

Demonceau, Albert .

COORDINATION CHEMISTRY REVIEWS, 2007, 251 (5-6) :765-794

[10] Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes [J].

Flanigan, Darrin M. ;

Romanov-Michailidis, Fedor ;

White, Nicholas A. ;

Rovis, Tomislav .

CHEMICAL REVIEWS, 2015, 115 (17) :9307-9387

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