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N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION

Year 2016, Volume: 3 Issue: 3, 93 - 104, 08.01.2017
https://doi.org/10.18596/jotcsa.90024

Abstract

A series of N-butyl substituted imidazolium salts, (1a-c) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes (2a-c) were synthesized and characterized. Pd-NHC complexes were fully determined by elemental analysis and spectroscopic. The synthesized complexes were tested in Suzuki-Miyaura cross-coupling reaction. These complexes were found to be efficient catalysts for the Suzuki-Miyaura reaction of phenylboronic acid with aryl bromides.

 

References

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  • Boehme C, Frenking G. Electronic structure of stable carbenes, silylenes, and germylenes. Journal of the American Chemical Society. 1996 Feb;118:2039-46. DOI: 10.1021/ja9527075.
  • Viciu M. S, Navarro O, Germaneau R. F, Kelly R. A, Sommer W, Marion N, Stevens E. D, Cavallo L, Nolan S. P. Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene). Organometallics. 2004 Feb;23:1629-35. DOI: 10.1021/om034319e.
  • a. Diez C, Nagel U. Chiral iridium(I) bis(NHC) complexes as catalysts for asymmetric transfer hydrogenation. Applied Organometallic Chemistry. 2010 Apr;24:509-516. DOI: 10.1002/aoc.1650. b. Crudden C. M, Allen D. P. Stability and reactivity of N-heterocyclic carbene complexes. Coordination Chemistry Reviews. 2004 Dec;248:2247-73. DOI: 10.1016/j.ccr.2004.05.013. c. Crabtree R. H. NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis. Journal of Organometallic Chemistry. 2005 Dec;690:5451-57. DOI: 10.1016/j.jorganchem.2005.07.099.
  • Herrmann W. A. N-Heterocyclic Carbenes: A new concept in organometallic catalysis. Angewandte Chemie International Edition. 2002 Apr;41:1290-1309. DOI: 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y.
  • Hahn F. E. Heterocyclic carbenes. Angewandte Chemie International Edition. 2006 Jan;45:1348-52. DOI: 10.1002/anie.200503858.
  • ArduengoIII A. J, Harlow R. L, Kline M. A stable crystalline carbene. Journal of the American Chemical Society. 1991 Jan;113:361-63. DOI: 10.1021/ja00001a054.
  • Mangalum A, McMillen C. D, Tennyson A. G. Synthesis, coordination chemistry and reactivity of transition metal complexes supported by a chelating benzimidazolylidene carboxylate ligand. Inorganica Chimica Acta. 2015 Feb;426:29-38. DOI: 10.1016/j.ica.2014.11.003.
  • Akkoç S, Gök Y, Akkurt M, Tahir M. N. Catalytic activities in the direct C5 arylation of novel palladium N-heterocyclic carbene complexes containing benzimidazol-2-ylidene nucleus. Inorganica Chimica Acta. 2014 Mar;413:221-30. DOI: 10.1016/j.ica.2014.01.015.
  • Serrano J. L, Pérez J, García L, Sánchez G, García J, Lozano P, Zende V, Kapdi A. N-Heterocyclic-Carbene complexes readily prepared from di-μ-hydroxopalladacycles catalyze the Suzuki Arylation of 9-bromophenanthrene. Organometallics. 2015 Jan;34:522-33. DOI: 10.1021/om501160n.
  • Lee J. Y, Ghosh D, Lee J. Y, Wu S. S, Hu C. H, Liu S. D, Lee H. M. Zwitterionic palladium complexes: Room-temperature Suzuki–Miyaura Cross-Coupling of sterically hindered substrates in an aqueous medium. Organometallics. 2014 Oct;33:6481-92. DOI: 10.1021/om500834y.
  • Hashmi A. S. K, Lothschütz C, Böhling C, Hengst T, Hubbert C, Rominger F. Carbenes made easy: Formation of unsymmetrically substituted N-heterocyclic carbene complexes of palladium(II), platinum(II) and gold(I) from coordinated isonitriles and their catalytic activity. Advanced Synthesis & Catalysis. 2010 Nov;352:3001-12. DOI: 10.1002/adsc.201000472.
  • Kong Y, Wen L, Song H, Xu S, Yang M, Liu B, Wang B. Synthesis, structures, and norbornene polymerization behavior of aryloxide-N-heterocyclic carbene ligated palladacycles. Organometallics. 2011 Dec;30:153-59. DOI: 10.1021/om100994s.
  • a. Doucet H. Suzuki–Miyaura Cross-Coupling Reactions of alkylboronic acid derivatives or alkyltrifluoroborates with aryl, alkenyl or alkyl halides and triflates. European Journal of Organic Chemistry. 2008 Feb;2008:2013-30. DOI: 10.1002/ejoc.200700984. b. Budarin V. L, Clark J. H, Luque R, Macquarrie D. J, White R. J. Palladium nanoparticles on polysaccharide-derived mesoporous materials and their catalytic performance in C–C coupling reactions. Green Chemistry. 2008 Oct;10:382-87. DOI: 10.1039/B715508E. c. Kotha S, Lahiri K, Kashinath D. Recent applications of the Suzuki—Miyaura Cross-Coupling Reaction in organic synthesis. Tetrahedron. 2002 Nov;58:9633-65. DOI:10.1016/S0040-4020(02)01188-2.
  • Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical Reviews. 1995 Nov;95:2457-83. DOI: 10.1021/cr00039a007.
  • Suzuki A. ChemInform Abstract: Recent Advances in the Cross-Coupling Reactions of Organoboron Derivatives with Organic Electrophiles. Journal of Organometallic Chemistry. 1999 Mar;576:147-68. DOI: 10.1016/S0022-328X(98)01055-9.
  • Stanforth S. P. Catalytic cross-coupling reactions in biaryl synthesis. Tetrahedron. 1998 Jan;54:263-303. DOI: 10.1016/S0040-4020(97)10233-2.
  • Whitcombe N. J, Hii K. K, Gibson S. E. Advances in the Heck chemistry of aryl bromides and chlorides. Tetrahedron. 2001 Aug;57:7449-76. DOI: 10.1016/S0040-4020(01)00665-2.
  • Crisp G.T. Variations on a theme—recent developments on the mechanism of the Heck reaction and their implications for synthesis. Chemical Society Reviews. 1998; 27:427-36. DOI: 10.1039/A827427Z.
  • O'Brien C. J, Kantchev E. A. B, Valente C, Hadei N, Chass G. A, Lough A, Hopkinson A. C, Organ M. G. Easily prepared air- and moisture-stable Pd–NHC (NHC=N-Heterocyclic Carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki–Miyaura Reaction. Chemistry A European Journal. 2006 Mar;12:4743-48. DOI: 10.1002/chem.200600251.
  • Ozdemir I, Gok Y, Ozeroglu O, Kaloglu M, Doucet H, Bruneau C. N-Heterocyclic Carbenes: Useful ligands for the palladium-catalysed direct C5 arylation of heteroaromatics with aryl bromides or electron-deficient aryl chlorides. European Journal of Inorganic Chemistry. 2010 Apr;2010:1798-1805. DOI: 10.1002/ejic.200901195.
  • Teci M, Brenner E, Matt D, Toupet L. N-Heterocyclic Carbenes Functioning as Monoligating Clamps. European Journal of Inorganic Chemistry. 2013 Mar;2013:2841-48. DOI: 10.1002/ejic.201300087.
Year 2016, Volume: 3 Issue: 3, 93 - 104, 08.01.2017
https://doi.org/10.18596/jotcsa.90024

Abstract

References

  • Jacobsen H, Correa A, Poater A, Costabile C, Cavallo L. Understanding the M(NHC) (NHC=N-heterocyclic carbene) bond. Coordination Chemistry Reviews. 2009 Mar;253:687-703. DOI: 10.1016/j.ccr.2008.06.006.
  • Boehme C, Frenking G. Electronic structure of stable carbenes, silylenes, and germylenes. Journal of the American Chemical Society. 1996 Feb;118:2039-46. DOI: 10.1021/ja9527075.
  • Viciu M. S, Navarro O, Germaneau R. F, Kelly R. A, Sommer W, Marion N, Stevens E. D, Cavallo L, Nolan S. P. Synthetic and structural studies of (NHC)Pd(allyl)Cl complexes (NHC = N-heterocyclic carbene). Organometallics. 2004 Feb;23:1629-35. DOI: 10.1021/om034319e.
  • a. Diez C, Nagel U. Chiral iridium(I) bis(NHC) complexes as catalysts for asymmetric transfer hydrogenation. Applied Organometallic Chemistry. 2010 Apr;24:509-516. DOI: 10.1002/aoc.1650. b. Crudden C. M, Allen D. P. Stability and reactivity of N-heterocyclic carbene complexes. Coordination Chemistry Reviews. 2004 Dec;248:2247-73. DOI: 10.1016/j.ccr.2004.05.013. c. Crabtree R. H. NHC ligands versus cyclopentadienyls and phosphines as spectator ligands in organometallic catalysis. Journal of Organometallic Chemistry. 2005 Dec;690:5451-57. DOI: 10.1016/j.jorganchem.2005.07.099.
  • Herrmann W. A. N-Heterocyclic Carbenes: A new concept in organometallic catalysis. Angewandte Chemie International Edition. 2002 Apr;41:1290-1309. DOI: 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO;2-Y.
  • Hahn F. E. Heterocyclic carbenes. Angewandte Chemie International Edition. 2006 Jan;45:1348-52. DOI: 10.1002/anie.200503858.
  • ArduengoIII A. J, Harlow R. L, Kline M. A stable crystalline carbene. Journal of the American Chemical Society. 1991 Jan;113:361-63. DOI: 10.1021/ja00001a054.
  • Mangalum A, McMillen C. D, Tennyson A. G. Synthesis, coordination chemistry and reactivity of transition metal complexes supported by a chelating benzimidazolylidene carboxylate ligand. Inorganica Chimica Acta. 2015 Feb;426:29-38. DOI: 10.1016/j.ica.2014.11.003.
  • Akkoç S, Gök Y, Akkurt M, Tahir M. N. Catalytic activities in the direct C5 arylation of novel palladium N-heterocyclic carbene complexes containing benzimidazol-2-ylidene nucleus. Inorganica Chimica Acta. 2014 Mar;413:221-30. DOI: 10.1016/j.ica.2014.01.015.
  • Serrano J. L, Pérez J, García L, Sánchez G, García J, Lozano P, Zende V, Kapdi A. N-Heterocyclic-Carbene complexes readily prepared from di-μ-hydroxopalladacycles catalyze the Suzuki Arylation of 9-bromophenanthrene. Organometallics. 2015 Jan;34:522-33. DOI: 10.1021/om501160n.
  • Lee J. Y, Ghosh D, Lee J. Y, Wu S. S, Hu C. H, Liu S. D, Lee H. M. Zwitterionic palladium complexes: Room-temperature Suzuki–Miyaura Cross-Coupling of sterically hindered substrates in an aqueous medium. Organometallics. 2014 Oct;33:6481-92. DOI: 10.1021/om500834y.
  • Hashmi A. S. K, Lothschütz C, Böhling C, Hengst T, Hubbert C, Rominger F. Carbenes made easy: Formation of unsymmetrically substituted N-heterocyclic carbene complexes of palladium(II), platinum(II) and gold(I) from coordinated isonitriles and their catalytic activity. Advanced Synthesis & Catalysis. 2010 Nov;352:3001-12. DOI: 10.1002/adsc.201000472.
  • Kong Y, Wen L, Song H, Xu S, Yang M, Liu B, Wang B. Synthesis, structures, and norbornene polymerization behavior of aryloxide-N-heterocyclic carbene ligated palladacycles. Organometallics. 2011 Dec;30:153-59. DOI: 10.1021/om100994s.
  • a. Doucet H. Suzuki–Miyaura Cross-Coupling Reactions of alkylboronic acid derivatives or alkyltrifluoroborates with aryl, alkenyl or alkyl halides and triflates. European Journal of Organic Chemistry. 2008 Feb;2008:2013-30. DOI: 10.1002/ejoc.200700984. b. Budarin V. L, Clark J. H, Luque R, Macquarrie D. J, White R. J. Palladium nanoparticles on polysaccharide-derived mesoporous materials and their catalytic performance in C–C coupling reactions. Green Chemistry. 2008 Oct;10:382-87. DOI: 10.1039/B715508E. c. Kotha S, Lahiri K, Kashinath D. Recent applications of the Suzuki—Miyaura Cross-Coupling Reaction in organic synthesis. Tetrahedron. 2002 Nov;58:9633-65. DOI:10.1016/S0040-4020(02)01188-2.
  • Miyaura N, Suzuki A. Palladium-catalyzed cross-coupling reactions of organoboron compounds. Chemical Reviews. 1995 Nov;95:2457-83. DOI: 10.1021/cr00039a007.
  • Suzuki A. ChemInform Abstract: Recent Advances in the Cross-Coupling Reactions of Organoboron Derivatives with Organic Electrophiles. Journal of Organometallic Chemistry. 1999 Mar;576:147-68. DOI: 10.1016/S0022-328X(98)01055-9.
  • Stanforth S. P. Catalytic cross-coupling reactions in biaryl synthesis. Tetrahedron. 1998 Jan;54:263-303. DOI: 10.1016/S0040-4020(97)10233-2.
  • Whitcombe N. J, Hii K. K, Gibson S. E. Advances in the Heck chemistry of aryl bromides and chlorides. Tetrahedron. 2001 Aug;57:7449-76. DOI: 10.1016/S0040-4020(01)00665-2.
  • Crisp G.T. Variations on a theme—recent developments on the mechanism of the Heck reaction and their implications for synthesis. Chemical Society Reviews. 1998; 27:427-36. DOI: 10.1039/A827427Z.
  • O'Brien C. J, Kantchev E. A. B, Valente C, Hadei N, Chass G. A, Lough A, Hopkinson A. C, Organ M. G. Easily prepared air- and moisture-stable Pd–NHC (NHC=N-Heterocyclic Carbene) complexes: A reliable, user-friendly, highly active palladium precatalyst for the Suzuki–Miyaura Reaction. Chemistry A European Journal. 2006 Mar;12:4743-48. DOI: 10.1002/chem.200600251.
  • Ozdemir I, Gok Y, Ozeroglu O, Kaloglu M, Doucet H, Bruneau C. N-Heterocyclic Carbenes: Useful ligands for the palladium-catalysed direct C5 arylation of heteroaromatics with aryl bromides or electron-deficient aryl chlorides. European Journal of Inorganic Chemistry. 2010 Apr;2010:1798-1805. DOI: 10.1002/ejic.200901195.
  • Teci M, Brenner E, Matt D, Toupet L. N-Heterocyclic Carbenes Functioning as Monoligating Clamps. European Journal of Inorganic Chemistry. 2013 Mar;2013:2841-48. DOI: 10.1002/ejic.201300087.
There are 22 citations in total.

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Journal Section Articles
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Rukiye Fırıncı This is me

Publication Date January 8, 2017
Submission Date July 1, 2016
Published in Issue Year 2016 Volume: 3 Issue: 3

Cite

Vancouver Fırıncı R. N-BUTYL SUBSTITUTED N-HETEROCYCLIC CARBENE-PD(II)-PYRIDINE (PEPPSI) COMPLEXES: SYNTHESIS, CHARACTERIZATION AND CATALYTIC ACTIVITY IN THE SUZUKI-MIYAURA REACTION. JOTCSA. 2017;3(3):93-104.