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Palladacyclic Complexes Containing C,N-Type Ligands as Catalysts in Cross-Coupling Reactions

  1. Ming-Tsz Chen,
  2. Chi-An Huang,
  3. Chi-Tien Chen

Article first published online: 10 JUN 2008

DOI: 10.1002/ejic.200800195

Issue

European Journal of Inorganic Chemistry

European Journal of Inorganic Chemistry

Volume 2008, Issue 20, pages 3142–3150, July 2008

Additional Information

How to Cite

Chen, M.-T., Huang, C.-A. and Chen, C.-T. (2008), Palladacyclic Complexes Containing C,N-Type Ligands as Catalysts in Cross-Coupling Reactions. Eur. J. Inorg. Chem., 2008: 3142–3150. doi: 10.1002/ejic.200800195

Author Information

  1. Department of Chemistry, National Chung Hsing University, Taichung 402, Taiwan, Republic of China

Publication History

  1. Issue published online: 10 JUL 2008
  2. Article first published online: 10 JUN 2008
  3. Manuscript Received: 22 FEB 2008

Funded by

  • National Science Council. Grant Number: NSC 95-2113-M-005-010-MY3
  • Ministry of Education, Taiwan, ROC

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Keywords:

  • Metallacycles;
  • N ligands;
  • Suzuki reaction;
  • Heck reaction;
  • Palladium

Abstract

Four ligand precursors, namely PhN=C(CMe2)(NPh)C=N(E) [E = –(CH2)2OMe (1); –(CH2)C(O)OMe (2); –(CH2)2CH3 (3);–C6H5 (4)], are described. Treatment of 1, 2, 3 or 4 with 1–1.1 molar equivalents of Pd(OAc)2 in THF or CH3CN affords the orthometallated palladium(II) complexes [{[PhN=C(CMe2)(N-η1-Ph)C=N(E)]Pd(OAc)}2] [E = –(CH2)2OMe (5); –(CH2)C(O)OMe (6); –(CH2)2CH3 (7); –C6H5 (8)], respectively. The reaction of 5 or 6 with an excess of NaCl(aq.) in acetoneaffords the orthometallated palladium(II) complexes [{PhN=C(CMe2)(N-η1-Ph)C=N(E)}PdCl] [E = –(CH2)2OMe (9); –(CH2)C(O)OMe (10)], whereas the reaction of 7 with an excess of NaCl(aq.) in acetone affords the dinuclear palladium(II) complex [{[PhN=C(CMe2)(N-η1-Ph)C=N(CH2)2CH3]PdCl}2] (11). The crystal and molecular structures of compounds 2, 4, 5, 7, 8 and 9 are reported The application of those novel palladacyclic complexes to the Suzuki and Heck reactions with aryl halide substrates is examined.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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