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Synthesis 2008(17): 2819-2824  
DOI: 10.1055/s-2008-1067199
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© Georg Thieme Verlag Stuttgart ˙ New York

N-Heterocyclic Carbene-Acetylamide Palladium Complexes and Their Catalytic Activities in Heck-Mizoroki Reactions

Tao Zhanga, Sijia Liua, Min Shi*a,b, Meixin Zhaoa
a Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. of China
Fax: +86(21)64166128; e-Mail: mshi@mail.sioc.ac.cn;
b State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China
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Publication History

Received 7 March 2008
Publication Date:
24 July 2008 (online)

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Abstract

A novel N-heterocyclic carbene-acetylamide ligand derived from binaphthyl-2,2′-diamine (BINAM) and its dinuclear NHC-Pd(II) complex as well as its corresponding complex bearing weakly coordinating acetate counterions, have been successfully synthesized in good yields. The dinuclear NHC-Pd(II) complex has been characterized by X-ray diffraction. Moreover, we found that these complexes are quite effective in Heck-Mizoroki reactions and give the corresponding products in good to excellent yields.

Key words

N-heterocyclic carbene-acetylamide - dinuclear NHC-Pd(II) complex - binaphthyl-2,2′-diamine - Heck-Mizoroki reaction

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10

The X-ray crystal data for compound 6 have been deposited in the CCDC with number 281153. Empirical formula: C28H19N3; Formula weight: 397.46; Crystal color, habit: colorless, prismatic; Crystal dimensions: 0.480 × 0.378 × 0.216 mm; Crystal system: monoclinic; Lattice type: primitive; Lattice parameters: a = 8.7871(8) Å, b = 25.373(3) Å, c = 9.3514(9) Å, β = 101.837(2)˚; V = 2040.6(3) ų; Space group: P21/c; Z = 4; D calc  = 1.294 g/cm³; F000 = 832; Diffractometer: Rigaku AFC7R; Residuals: R1, wR2: 0.0548, 0.1023.

11

The X-ray crystal data of NHC-Pd(II) complex 7 have been deposited in the CCDC with number 601088. Empirical formula: C60H48I2N6O2Pd2; Formula weight: 1383.64; Crystal color, habit: colorless, prismatic; Crystal dimensions: 0.138 × 0.115 × 0.040 mm; Crystal system: monoclinic; Lattice type: primitive; Lattice parameters: a = 14.496(12) Å, b = 20.803(16) Å, c = 23.523(19) Å, β = 101.179(15)˚; V = 6959(10) ų; Space group: P21/c; Z = 4; D calc  = 1.321 g/cm³; F000 = 2720; Diffractometer: Rigaku AFC7R; Residuals: R1, wR2: 0.1167, 0.2771.