Synthesis of palladium complexes with bis(diphenylphosphinomethyl) amino ligands: A catalyst for the Heck reaction of aryl halide with methyl acrylate

被引：31

作者：

Keles, Mustafa ^{[1
]}

Aydin, Ziya ^{[1
]}

Serindag, Osman ^{[1
]}

机构：

[1] Cukurova Univ, Fac Sci & Letters, Dept Chem, TR-01330 Adana, Turkey

来源：

JOURNAL OF ORGANOMETALLIC CHEMISTRY | 2007年 / 692卷 / 10期

关键词：

bis(diphenylphosphinomethyl)amino; Pd complex; Heck reaction; aryl halide;

D O I：

10.1016/j.jorganchem.2007.01.003

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A series of ligands, (Ph2PCH2)(2)NR (R = -CH3) (1), -C(CH3)(3), (2) -m-C6H4SO3Na (3), and their Pd(II) complexes have been synthesized under nitrogen atmosphere using Schlenk method. All compounds were characterized using elemental analysis and spectroscopic techniques (AAS, NMR (H-1, P-31)). Based on the analysis the complexes have been proposed as in square planar geometry. The Pd(II) complexes were applied to the Heck reaction of aryl halide (Br, Cl) with methyl acrylate. The results have exhibited that complexes [PdCl2((Ph2PCH2)(2)NCH3)] (4) and [PdCl2((Ph2PCH2)(2)NC(CH3)(3))] (5) have shown higher turnover numbers (TON) than complex [PdCl2(Ph2PCH2)(2)N-m-C6H4SO3Na] (6). (c) 2007 Elsevier B.V. All rights reserved.

引用

页码：1951 / 1955

页数：5

共 24 条

[11] Recyclable polymer-supported Pd catalysts for aryl amination reactions [J].

Guinó, M ;

Hii, KK .

TETRAHEDRON LETTERS, 2005, 46 (43) :7363-7366

[12] Synthesis of metal complexes of peptide-phosphinites: Metal complexes in asymmetric Heck reaction [J].

Jayasinghe, Dushmanthi ;

Kraatz, Heinz-Bernhard .

INORGANICA CHIMICA ACTA, 2006, 359 (09) :3054-3065

[13] A palladium complex with a new hemilabile amino- and sulfur-containing phosphinite ligand as an efficient catalyst for the Heck reaction of aryl bromides with styrene. The effect of the amino group [J].

Kostas, ID ;

Steele, BR ;

Terzis, A ;

Amosova, SV .

TETRAHEDRON, 2003, 59 (19) :3467-3473

[14] Synthesis of new rhodium complexes with a hemilabile nitrogen-containing bis(phosphinite) or bis(phosphine) ligand. Application to hydroformylation of styrene [J].

Kostas, ID .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 626 (1-2) :221-226

[15] Nickel complexes catalyzed Heck reaction of iodobenzene and methyl acrylate [J].

Ma, SY ;

Wang, HJ ;

Gao, KM ;

Zhao, FY .

JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 248 (1-2) :17-20

[16] Influence of the catalytic conditions on the selectivity of the Pd-catalyzed Heck arylation of acrolein derivatives [J].

Noel, Sebastein ;

Djakovitch, Laurent ;

Pinel, Catherine .

TETRAHEDRON LETTERS, 2006, 47 (23) :3839-3842

[17] Examination of ligand effects in the Heck arylation reaction [J].

Qadir, M ;

Möchel, T ;

Hii, KK .

TETRAHEDRON, 2000, 56 (40) :7975-7979

[18] Palladium(II) complexes with phosphorus-nitrogen mixed donors. Efficient catalysts for the Heck reaction [J].

Reddy, KR ;

Surekha, K ;

Lee, GH ;

Peng, SM ;

Liu, ST .

ORGANOMETALLICS, 2000, 19 (13) :2637-2639

[19] Substituent effects in the rhodium-catalyzed hydroformylation of olefins using bis(diarylphosphino)methylamino ligands [J].

Reetz, MT ;

Waldvogel, SR ;

Goddard, R .

TETRAHEDRON LETTERS, 1997, 38 (34) :5967-5970

[20] SYNTHESIS OF A CROWN-ETHER FUNCTIONALIZED PHOSPHINE AND ITS NICKEL(II), PALLADIUM(II) AND PLATINUM(II) COMPLEXES [J].

SERINDAG, O .

SYNTHESIS AND REACTIVITY IN INORGANIC AND METAL-ORGANIC CHEMISTRY, 1995, 25 (02) :327-335

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