Abnormal NHC palladium complexes: Synthesis, structure, and reactivity

Current Organic Chemistry

Volumn 15, Issue 18, 2011, Pages 3325-3336

  Poulain, Aurelie ^b   Iglesias, Manuel ^a,b   Albrecht, Martin ^a,b  

^a UNIVERSITY COLLEGE DUBLIN   (Ireland)

^b UNIVERSITY OF FRIBOURG   (Switzerland)

Author keywords

Abnormal bonding mode; Bonding mode analysis; Catalysis; Ligand induced reactivity; N heterocyclic carbenes; Palladium; Selective bond activation

Indexed keywords

CATALYSIS; CATALYST ACTIVITY; CHELATION; CHEMICAL BONDS; ORGANIC COMPOUNDS; PALLADIUM COMPOUNDS; SYNTHESIS (CHEMICAL);

ABNORMAL BONDING MODE; BOND ACTIVATION; BONDING MODE ANALYSE; BONDING MODES; LIGAND-INDUCED REACTIVITY; MODE ANALYSIS; N-HETEROCYCLIC CARBENES; PALLADIUM CHEMISTRY; SELECTIVE BOND ACTIVATION;

LIGANDS;

EID: 80052511143     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211797248049     Document Type: Article

References (86)

1. Tavenor, R. Palladio and Palladianism; Thames and Hudson: London, UK, 1991.
2. Wollaston, W. H. Phil. Trans. R. Soc. Lond., 1804, 94, 419.
3. Wollaston, W. H. Phil. Trans. R. Soc. Lond., 1805, 95, 316.
4. de Meijere, A.; Diederich, F. (Eds.), Metal-Catalzyed Cross-Coupling Reactions; Wiley-VCH: Weinheim, Germany, 2004.
5. Dupont, J.; Pfeffer, M. (Eds.), Palladacycles; Wiley-VCH: Weinheim, Germany, 2008.
6. Nolan, S. P. (Ed.), N-Heterocyclic Carbenes in Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
7. Diez-Gonzalez, S. (Ed.), N-Heterocyclic Carbenes: From Laboratories Curiosities to Efficient Synthetic Tools; Royal Society of Chemistry: Cambridge, UK, 2011.
8. Gründemann, S.; Kovacevic, A.; Albrecht, M.; Faller, J. W.; Crabtree, R. H. Abnormal binding in a carbene complex formed from an imidazolium salt and a metal hydride complex. Chem. Commun., 2001, 2274.
9. Abnormal pyridylidene palladium complexes have been prepared as early as 1980 by protonation of a 3-pyridyl palladium complex at nitrogen, though these complexes have not been recognized as carbene-type complexes.
10. Isobe, K.; Kai, E.; Nakamura, Y.; Nishimoto, K.; Miwa, T.; Kawaguchi, S.; Kinoshita, K.; Nakatsu, K. trans-Bromo(2-, 3-, and 4-pyridyl)- bis(triethylphosphine)palladium(II) complexes. J. Am. Chem. Soc., 1980, 102, 2475.
11. Albrecht, M. C4-bound imidazolylidenes: from curiosities to high-impact carbene ligands. Chem. Commun., 2008, 3601.
12. Schuster, O.; Yang, L.; Raubenheimer, H. G.; Albrecht, M. Beyond conventional N-heterocyclic carbenes: Abnormal, remote, and other classes of NHC ligands with reduced heteroatom stabilization. Chem. Rev., 2009, 109, 3445.
13. Albrecht, M. Carbenes in action. Science, 2009, 326, 532.
14. Albrecht, M. Abnormal carbenes as ligands in transition metal chemistry: Curiosities with exciting perspectives. Chimia, 2009, 63, 105.
15. Arnold, P. L.; Pearson, S. Abnormal N-heterocyclic carbenes. Coord. Chem. Rev., 2007, 251, 596.
16. Krüger, A.; Albrecht, M. In: N-Heterocyclic Carbenes: From Laboratories Curiosities to Efficient Synthetic Tools; Diez-Gonzalez, S., Ed.; Royal Society of Chemistry: Cambridge, UK, 2011.
17. Lalrempuia, R.; McDaniel, N. D.; Müller-Bunz, H.; Bernhard, S.; Albrecht, M. Angew. Chem., Int. Ed., 2010, 49, 9765.
18. Prades, A.; Peris, E.; Albrecht, M. Organometallics, 2011, 30, 1162.
19. IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"), compiled by McNaught A. D.; Wilkinson, A., compilors; Blackwell Scientific Publications: Oxford, UK, 1997).
20. The same dichotomy exists in Fischer carbene complexes, which are actually better described as zwitterionic species rather than as carbene complexes.
21. Melaimi, M.; Sloeilhavoup, M.; Bertrand, G. Stable cyclic carbenes and related species beyond diaminocarbenes. Angew. Chem., Int. Ed., 2010, 49, 8810.
22. Piro, N. A.; Owen, J. S.; Bercaw, J. E. Pyridinium-derived N-heterocyclic carbene ligands: Syntheses, structures and reactivity of N-(2'- pyridyl)pyridin-2-ylidene complexes of nickel(II), palladium(II) and platinum(II). Polyhedron, 2004, 23, 2797.
23. Dholakia, S.; Gillard, R. D.; Wimmer, F. L. N-methyl-2,2'-bipyridylium complexes: synthesis and cyclometallation of M(bpyMe)X3 (M = Pt, Pd; X = Cl, Br). Inorg. Chim. Acta, 1983, 69, 179.
24. Wimmer, S.; Wimmer, F. L. Influence of the length of the quaternisation group on the cyclometallation of [M(2,4'-R-bipy)Cl3] (M = PtII or PdII; 2,4'-R-bipy = 1'-alkyl-2,4'- bipyridinium). J. Chem. Soc., Dalton Trans., 1994, 879.
25. Heckenroth, M.; Kluser, E.; Neels, A.; Albrecht, M. Palladation of diimidazolium salts at the C4 position: Access to remarkably electron-rich palladium(ii) centers. Dalton Trans., 2008, 6242.
26. Heckenroth, M.; Kluser, E.; Neels, A.; Albrecht, M. Neutral ligands with exceptional donor ability for palladium-catalyzed alkene hydrogenation. Angew. Chem., Int. Ed., 2007, 46, 6293.
27. Albrecht, M. Cyclometalation Using d-Block Transition Metals: Fundamental Aspects and Recent Trends. Chem. Rev., 2010, 110, 576.
28. Heckenroth, M.; Neels, A.; Garnier, M. G.; Aebi, P.; Ehlers, A. W.; Albrecht, M. On the electronic impact of abnormal C4-bonding in nheterocyclic carbene complexes. Chem. Eur. J., 2009, 15, 9375.
29. Kong, Y.; Ren, H.; Xu, S.; Song, H.; Liu, B.; Wang, B. Synthesis, Structures, and Norbornene Polymerization Behavior of Bis(aryloxide-N-heterocyclic carbene) Palladium Complexes. Organometallics, 2009, 28, 5934.
30. This effect has been demonstrated also for other metals, see for example: Ellul, C. E.; Mahon, M. F.; Saker, O.; Whittlesey, M. K. Abnormally bound N-heterocyclic carbene complexes of ruthenium: C-H activation of both C4 and C5 positions in the same ligand. Angew. Chem., Int. Ed., 2007, 46, 6343.
31. Baya, M.; Eguillor, B.; Esteruelas, M. A.; Olivan, M.; Onate, E. Influence of the anion of the salt used on the coordination mode of an N-heterocyclic carbene ligand to osmium. Organometallics, 2007, 26, 6556.
32. Appelhans, L. N.; Zuccaccia, D.; Kovacevic, A.; Chianese, A. R.; Miecznikowski, J. R.; Macchioni, A.; Clot, E.; Eisenstein, O.; Crabtree, R. H. An Anion-Dependent Switch in Selectivity Results from a Change of C-H Activation Mechanism in the Reaction of an Imidazolium Salt with IrH5(PPh3)2. J. Am. Chem. Soc., 2005, 127, 16299.
33. Scheele, U. J.; Dechert, S.; Meyer, F. Non-innocence of N-heterocyclic carbene ligands: Intermolecular C-H activation in allyl palladium NHC complexes. Chem. Eur. J., 2008, 14, 5112.
34. Wimmer, F. L.; Wimmer, S. N-methyl-2,2'-bipyridylium ion (bpyMe) complexes: Synthesis and cyclometallation of [Pd(bpyMe)2Cl2]2+. Polyhedron, 1985, 4, 1665.
35. Castan, P.; Dahan, F.; Wimmer, S.; Wimmer, F. L. The mode of coordination of the quaternised 2,4'-bipyridinium cation. Crystal structures of trichloro(1'-methyl-2,4'-bipyridinium-χN 1)platinum(II) dihydrate and dichloro(1'-methyl-2,4'-bipyridin-3'-ylium-χC 3', N1)platinum(II). J. Chem. Soc., Dalton Trans., 1990, 2971.
36. Labiad, B.; Villemin, D.; Wimmer, F. L.; Wimmer, S. Solid-state cyclometallation of the 1-methyl-2,4'-bipyridinium complexes of palladiumII and platinumII. J. Organomet. Chem., 1994, 479, 153.
37. Araki, S.; Wanibe, Y.; Uno, F.; Morikawa, A.; Yamamoto, K.; Chiba, K.; Butsugan, Y. Synthesis and Chemical Transformations of 1,3- Diaryltetrazolium Salts. Preparation of Mercury(II) and Palladium(II) Complexes of 1,3-Diaryltetrazolylene and Reactions of 5-Substituted 1,3- Diphenyltetrazolium Salts with Nucleophiles. Chem. Ber., 1993, 126, 1149.
38. Iglesias, M.; Albrecht, M. unpublished.
39. Stander, E.; Schuster, O.; Heydenrych, G.; Cronje, S.; Tosh, E.; Albrecht, M.; Frenking, G.; Raubenheimer, H. G. Organometallics, 2010, 29, 5721.
40. Karthikeyan, T.; Sankararaman, S. Palladium complexes with abnormal Nheterocyclic carbene ligands derived from 1, 2, 3-triazolium ions and their application in Suzuki coupling. Tetrahedron Lett., 2009, 50, 5834.
41. Poulain, A.; Canseco-Gonzalez, D.; Hynes-Roche, R.; Müller-Bunz, H.; Schuster, O.; Stoeckli-Evans, H.; Neels, A.; Albrecht, M. Organometallics, 2011, 30, 1021.
42. Aldeco-Perez, E.; Rosenthal, A. J.; Donnadieu, B.; Parameswaran, P.; Frenking, G.; Bertrand, G. Isolation of a C5-deprotonated Imidazolium, a crystalline Abnormal N-Heterocyclic Carbene. Science, 2009, 326, 556.
43. Lavallo, V.; Dyker, C. A.; Donnadieu, B.; Bertrand, G. Synthesis and ligand properties of stable five-membered-ring allenes containing only second-row elements. Angew. Chem., Int. Ed., 2008, 47, 5411.
44. Lavallo, V.; Canac, Y.; Präsang, C.; Donnadieu, B.; Bertrand, G. Stable cyclic (alkyl)(amino)carbenes as rigid or flexible, bulky, electron-rich ligands for transition-metal catalysts: A quaternary carbon atom makes the difference. Angew. Chem., Int. Ed., 2005, 44, 5705.
45. Lavallo, V.; Canac, Y.; DeHope, A.; Donnadieu, B.; Bertrand, G. A rigid cyclic (alkyl)(amino)carbene ligand leads to isolation of low-coordinate transitionmetal complexes. Angew. Chem., Int. Ed., 2005, 44, 7236.
46. Fernandez, I.; Dyker, C. A.; DeHope, A.; Donnadieu, B.; Frenking, G.; Bertrand, G. Exocyclic delocalization at the expense of aromaticity in 3,5- bis(Π-donor) substituted pyrazolium ions and corresponding cyclic bent allenes. J. Am. Chem. Soc., 2009, 131, 11875.
47. Tonner, R.; Heydenrych, G.; Frenking, G. Bonding analysis of N-heterocyclic carbene tautomers and phosphine ligands in transition-metal complexes: A theoretical study. Chem. Asian J., 2007, 2, 1555.
48. Holloczki, O.; Nyulaszi, L. Stabilizing the hammick intermediate. J. Org. Chem., 2008, 73, 4794.
49. Nakafuji, S.; Kobayashi, J.; Kawashima, T. Generation and coordinating properties of a carbene bearing a phosphorus ylide: An intensely electrondonating ligand. Angew. Chem., Int. Ed., 2008, 47, 1141.
50. Kluser, E.; Neels, A.; Albrecht, M. Mild and rational synthesis of palladium complexes comprising C(4)-bound N-heterocyclic carbenes. Chem. Commun., 2006, 4495.
51. Lebel, H.; Janes, M. K.; Charrette, A. B.; Nolan, S. P. Structure and Reactivity of Unusual N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts. J. Am. Chem. Soc., 2004, 126, 5046.
52. Paulson, M.; Neels, A.; Albrecht, M. 1,2,3-Triazolylidenes as Versatile Abnormal Carbene Ligands for Late Transition Metals. J. Am. Chem. Soc., 2008, 130, 13534.
53. Han, Y.; Huynh, H. V. Preparation and characterization of the first pyrazole- based remote N-heterocyclic carbene complexes of palladium(II). Chem. Commun., 2007, 1089.
54. Han, Y.; Huynh, H. V.; Tan, G. K. Palladium(II) pyrazolin-4-ylidenes: Remote N-heterocyclic carbene complexes and their catalytic application in aqueous Suzuki-Miyaura coupling. Organometallics, 2007, 26, 6581.
55. Han, Y.; Lee, L. J.; Huynh, H. V. Palladium(II) pyrazolin-4-ylidenes: Substituent effects on the formation and catalytic activity of pyrazole-based remote NHC complexes. Organometallics, 2009, 28, 2778.
56. Castan, P.; Jaud, J.; Wimmer, S.; Wimmer, F. L. Notes. Aqueous chemistry of platinum and palladium complexes. Synthesis and crystal structure of a palladium(II) aqua complex with a cyclometallated ligand: [PdL(H2O)(ONO2)]ClO4•H2O (L = 1-methyl-2,2'-bipyridin-3-ylium). J. Chem. Soc., Dalton Trans., 1991, 1155.
57. Iglesias, M.; Albrecht, M. Expanding the family of mesoionic complexes: Donor properties and catalytic impact of palladated isoxazolylidenes. Dalton Trans., 2010, 39, 5213.
58. The inverse trend is observed when analyzing the Pd-Cl trans bond, which increases along the series C2-pyridylidene < C3-pyridylidene < C4- pyridylidene, and it has been suggested
59. that the bond strength and the trans influence correlate in this triad.
60. Mercs, L.; Neels, A.; Albrecht, M. Probing the potential of N-heterocyclic carbenes in molecular electronics: Redox-active metal centers interlinked by a rigid ditopic carbene ligand. Dalton Trans., 2008, 5570.
61. Heydenrych, G.; von Hopffgarten, M.; Stander, E.; Schuster, O.; Raubenheimer, H. G.; Frenking, G. The nature of the metal-carbene bond in normal and abnormal pyridylidene, quinolylidene and isoquinolylidene complexes. Eur. J. Inorg. Chem., 2009, 1892.
62. For examples, see: Würtz, S.; Glorius, F. Surveying sterically demanding N-heterocyclic carbene ligands with restricted flexibility for palladiumcatalyzed cross-coupling reactions. Acc. Chem. Res., 2008, 41, 1523.
63. Poater, A.; Cosenza, B.; Correa, A.; Giudice, S.; Ragone, F.; Scarone, V.; Cavallo, L. SambVca: A web application for the calculation of the buried volume of N-heterocyclic carbene ligands. Eur. J. Inorg. Chem., 2009, 1759.
64. Organ, M. G.; Calimsiz, S.; Sayah, M.; Hoi, K. H.; Lough, A. J. Pd- PEPPSI-IPent: An Active, Sterically Demanding Cross-Coupling Catalystand its application in the synthesis of tetra-ortho-substituted biaryls. Angew. Chem., Int. Ed., 2009, 48, 2383.
65. Organ, M. G.; Chass, G. A.; Fang, D.-C.; Hopkinson, A. C.; Valente, C. Pd-NHC (PEPPSI) complexes: Synthetic utility and computational studies into their reactivity. Synthesis, 2008, 17, 2776.
66. Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. N-heterocyclic carbenes in late transition metal catalysis. Chem. Rev., 2009, 109, 3612.
67. Chinaese, A. R.; Kovacevic, A.; Zeglis, B. M.; Faller, J. W.; Crabtrees, R. H. Abnormal C5-bound N-heterocyclic carbenes: Extremely strong electron donor ligands and their iridium(I) and iridium(III) complexes. Organometallics, 2004, 23, 2461.
68. Kelly, R. A.; Clavier, H.; Giudice, S., Scott, N. M.; Stevens, E. D.; Bordner, J.; Samardjiev, I.; Hoff, C. D.; Cavallo, L.; Nolan, S. Determination of N-heterocyclic carbene (NHC) steric and electronic parameters using the [(NHC)Ir(CO)2Cl] system. Organometallics, 2008, 27, 202.
69. Tolman, C.A. Steric effects of phosphorus ligands in organometallic chemistry and homogeneous catalysis. Chem. Rev., 1977, 77, 313.
70. CO stretch vibrations may not always be reliable as they may be strongly affected by stereoelectronic effects, see for example: Fürstner, A.; Alcarazo, M.; Krause, H.; Lehmann, C. W. Effective modulation of the donor properties of n-heterocyclic carbene ligands by Through-space communication within a planar chiral scaffold. J. Am. Chem. Soc., 2007, 129, 12676.
71. Song, G.; Zhang, Y.; Li, X. Rhodium(I)-(N-heterocyclic carbene)- diphosphine complexes. Organometallics, 2008, 27, 1936.
72. Kuchenbeiser, G.; Soleilhavoup, M.; Donnadieu, B.; Bertrand, G. Reactivity of cyclic (Alkyl)(amino)carbenes (CAACs) and Bis(amino)cyclopropenylidenes (BACs) with Heteroallenes: Comparisons with their N-heterocyclic carbene (NHCs) counterparts. Chem. Asian J., 2009, 4, 1745.
73. Mercs, L.; Labat, G.; Neels, A.; Ehlers, A.; Albrecht, M. Piano-stool iron(II) complexes as probes for the bonding of N-heterocyclic carbenes: Indications for ��-acceptor ability. Organometallics, 2006, 25, 5648.
74. Lever, A. B. P. Electrochemical parametrization of metal complex redox potentials, using the ruthenium(III)/ruthenium(II) couple to generate a ligand electrochemical series. Inorg. Chem., 1990, 29, 1271.
75. Buscemi, G.; Basato, M.; Biffis, A.; Gennaro, A.; Isse, A. A.; Natile, M. M.; Tubaro, C. Electronic properties of chelating dicarbene palladium complexes: A combined electrochemical, NMR and XPS investigation. J. Organomet. Chem., 2010, in press.
76. Tapu, D.; Dixon, D. A.; Roe, C. 13C NMR spectroscopy of Arduengo-type carbenes and their derivatives. Chem. Rev., 2009, 109, 3385.
77. Huynh, H. V.; Han, Y.; Jothibasu, R.; Yang, J. A. 13C NMR spectroscopic determination of ligand donor strengths using N-Heterocyclic carbene complexes of palladium(II). Organometallics, 2009, 28, 5395.
78. Tukov, A. A.; Normand, A. T.; Nechaev, M. S. N-heterocyclic carbenes bearing two, one and no nitrogen atoms at the ylidene carbon: Insight from theoretical calculations. Dalton Trans., 2009, 7015.
79. Gusev, D. G. Electronic and steric parameters of 76 N-heterocyclic carbenes in Ni(CO)3(NHC). Organometallics, 2009, 28, 6458.
80. Cavell, K. J.; McGuinness, D. S. Redox processes involving hydrocarbylmetal (N-heterocyclic carbene) complexes and associated imidazolium salts: Ramifications for catalysis. Coord. Chem. Rev., 2004, 248, 671.
81. Crudden, C. M.; Allen, D. P. Stability and reactivity of N-heterocyclic carbene complexes. Coord. Chem. Rev., 2004, 248, 2247.
82. Lee, M.-T.; Lee, H. M.; Hu, C.-H. A theoretical study of the Heck reaction: N-heterocyclic carbene versus phosphine ligands. Organometallics, 2007, 26, 1317.
83. Li, Z.; Fu, Y.; Guo, Q.-X.; Liu, L. Theoretical Study on Monoligated Pd- Catalyzed CrossCoupling Reactions of Aryl Chlorides and Bromides. Organometallics. Organometallics, 2008, 27, 4043.
84. Barrios-Landeros, F.; Carrow, B. P.; Hartwig, J. F. Effect of ligand steric properties and halide identity on the mechanism for oxidative addition of haloarenes to trialkylphosphine Pd(0) complexes. J. Am. Chem. Soc., 2009, 131, 8141.
85. John, A.; Shaikh, M. M.; Ghosh, P. Palladium Complexes of Abnormal Nheterocyclic Carbenes as Precatalysts for the Much-Preferred Cu-Free and Amine-Free Sonogashira Coupling in Air in a Mixed Aqueous Medium. Dalton Trans., 2009, 10581.
86. Yang, Y.; Huang, An X- (X = I, Br)-Triggered Ring-Opening Cyclization of Cyclopropenyl-Substituted Alkyl Halides or Mesylates: An Efficient and Highly Regio- and Stereoselective Approach to (E)-Haloalkylidene 4-7- Membered Cyclic Compounds. X. Synlett, 2008, 1366.