Palladium(II) complexes of readily functionalized bidentate 2-pyridyl-1,2,3-triazole "click" ligands: A synthetic, structural, spectroscopic, and computational study

Inorganic Chemistry

Volumn 50, Issue 13, 2011, Pages 6334-6346

  Kilpin, Kelly J ^a   Gavey, Emma L ^a   McAdam, C John ^a   Anderson, Christopher B ^a   Lind, Samuel J ^a,b   Keep, Courtney C ^a   Gordon, Keith C ^a,b   Crowley, James D ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b MACDIARMID INSTITUTE FOR ADVANCED MATERIALS AND NANOTECHNOLOGY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; ORGANOMETALLIC COMPOUND; PALLADIUM; TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CLICK CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; QUANTUM THEORY; STEREOISOMERISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

CLICK CHEMISTRY; CRYSTALLOGRAPHY, X-RAY; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; QUANTUM THEORY; STEREOISOMERISM; TRIAZOLES;

EID: 79959707341     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic200789b     Document Type: Article

References (202)

1. Yamada, T. New Front. Asymmetric Catal. 2007, 33-58
2. Shintani, R.; Hayashi, T. New Front. Asymmetric Catal. 2007, 59-100
3. Ohkuma, T.; Kitamura, M.; Noyori, R. New Front. Asymmetric Catal. 2007, 1-32
4. Rach, S. F.; Kuehn, F. E. Chem. Rev. 2009, 109, 2061-2080
5. Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612-3676
6. Daugulis, O.; Do, H.-Q.; Shabashov, D. Acc. Chem. Res. 2009, 42, 1074-1086
7. Rasappan, R.; Laventine, D.; Reiser, O. Coord. Chem. Rev. 2008, 252, 702-714
8. Gupta, K. C.; Sutar, A. K. Coord. Chem. Rev. 2008, 252, 1420-1450
9. Gruetzmacher, H. Angew. Chem., Int. Ed. 2008, 47, 1814-1818
10. Correa, A.; Garcia Mancheno, O.; Bolm, C. Chem. Soc. Rev. 2008, 37, 1108-1117
11. Kempe, R. Chem.-Eur. J. 2007, 13, 2764-2773
12. Sandee, A. J.; Reek, J. N. H. Dalton Trans. 2006, 3385-3391
13. Wilkinson, M. J.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Org. Biomol. Chem. 2005, 3, 2371-2383
14. Donnelly, P. S. Dalton Trans. 2011, 40, 999-1010
15. Hartinger, C. G.; Dyson, P. J. Chem. Soc. Rev. 2009, 38, 391-401
16. Hannon, M. J. Pure Appl. Chem. 2007, 79, 2243-2261
17. Che, C.-M.; Siu, F.-M. Curr. Opin. Chem. Biol. 2010, 14, 255-261
18. Sun, R. W.-Y.; Che, C.-M. Coord. Chem. Rev. 2009, 253, 1682-1691
19. Wai-Yin Sun, R.; Ma, D.-L.; Wong, E. L.-M.; Che, C.-M. Dalton Trans. 2007, 4884-4892
20. Mewis, R. E.; Archibald, S. J. Coord. Chem. Rev. 2010, 254, 1686-1712
21. Metzler-Nolte, N. Top. Organomet. Chem. 2010, 32, 195-217
22. Ducani, C.; Leczkowska, A.; Hodges, N. J.; Hannon, M. J. Angew. Chem., Int. Ed. 2010, 49, 8942-8945
23. Sanchez-Cano, C.; Hannon, M. J. Dalton Trans. 2009, 10702-10711
24. Cardo, L.; Hannon, M. J. Inorg. Chim. Acta 2009, 362, 784-792
25. Hannon, M. J. Chem. Soc. Rev. 2007, 36, 280-295
26. Hamblin, J.; Tuna, F.; Bunce, S.; Childs, L. J.; Jackson, A.; Errington, W.; Alcock, N. W.; Nierengarten, H.; Van Dorsselaer, A.; Leize-Wagner, E.; Hannon, M. J. Chem.-Eur. J. 2007, 13, 9286-9296
27. Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; White, J. M. Inorg. Chem. 2005, 45, 496-498
28. Holland, J. P.; Aigbirhio, F. I.; Betts, H. M.; Bonnitcha, P. D.; Burke, P.; Christlieb, M.; Churchill, G. C.; Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; Green, J. C.; Peach, J. M.; Vasudevan, S. R.; Warren, J. E. Inorg. Chem. 2006, 46, 465-485
29. Xiao, Z.; Donnelly, P. S.; Zimmermann, M.; Wedd, A. G. Inorg. Chem. 2008, 47, 4338-4347
30. Paterson, B. M.; Karas, J. A.; Scanlon, D. B.; White, J. M.; Donnelly, P. S. Inorg. Chem. 2010, 49, 1884-1893
31. Paterson, B. M.; White, J. M.; Donnelly, P. S. Dalton Trans. 2010, 39, 2831-2837
32. Chi, Y.; Chou, P.-T. Chem. Soc. Rev. 2010, 39, 638-655
33. Qian, X.; Xiao, Y.; Xu, Y.; Guo, X.; Qian, J.; Zhu, W. Chem. Commun. 2010, 46, 6418-6436
34. Fernandez-Moreira, V.; Thorp-Greenwood, F. L.; Coogan, M. P. Chem. Commun. 2010, 46, 186-202
35. Canary, J. W.; Mortezaei, S.; Liang, J. Coord. Chem. Rev. 2010, 254, 2249-2266
36. Kumar, A.; Sun, S.-S.; Lees, A. J. Coord. Chem. Rev. 2008, 252, 922-939
37. Amijs, C. H. M.; van Klink, G. P. M.; van Koten, G. Dalton Trans. 2006, 308-327
38. Thanasekaran, P.; Liao, R.-T.; Liu, Y.-H.; Rajendran, T.; Rajagopal, S.; Lu, K.-L. Coord. Chem. Rev. 2005, 249, 1085-1110
39. Murphy, L.; Williams, J. A. G. Top. Organomet. Chem. 2010, 28, 75-111
40. Williams, J. A. G. Chem. Soc. Rev. 2009, 38, 1783-1801
41. Wiester, M. J.; Ulmann, P. A.; Mirkin, C. A. Angew. Chem., Int. Ed. 2011, 50, 114-137
42. Lusby, P. J. Annu. Rep. Prog. Chem., Sect. A Inorg. Chem. 2010, 106, 319-339
43. Han, Y.-F.; Li, H.; Jin, G.-X. Chem. Commun. 2010, 46, 6879-6890
44. Northrop, B. H.; Zheng, Y.-R.; Chi, K.-W.; Stang, P. J. Acc. Chem. Res. 2009, 42, 1554-1563
45. Li, S.-S.; Northrop, B. H.; Yuan, Q.-H.; Wan, L.-J.; Stang, P. J. Acc. Chem. Res. 2009, 42, 249-259
46. Halcrow, M. A. Dalton Trans. 2009, 2059-2073
47. Steel, P. J.; Fitchett, C. M. Coord. Chem. Rev. 2008, 252, 990-1006
48. Perez, J.; Riera, L. Chem. Soc. Rev. 2008, 37, 2658-2667
49. Northrop, B. H.; Yang, H.-B.; Stang, P. J. Chem. Commun. 2008, 5896-5908
50. Miyashita, N.; Kurth, D. G. J. Mater. Chem. 2008, 18, 2636-2649
51. Glasson, C. R. K.; Lindoy, L. F.; Meehan, G. V. Coord. Chem. Rev. 2008, 252, 940-963
52. Dalgarno, S. J.; Power, N. P.; Atwood, J. L. Coord. Chem. Rev. 2008, 252, 825-841
53. Cooke, M. W.; Chartrand, D.; Hanan, G. S. Coord. Chem. Rev. 2008, 252, 903-921
54. Ward, M. D. Chem. Commun. 2009, 4487-4499
55. Durola, F.; Sauvage, J.-P.; Wenger, O. S. Coord. Chem. Rev. 2010, 254, 1748-1759
56. Credi, A.; Venturi, M.; Balzani, V. ChemPhysChem 2010, 11, 3398-3403
57. Kay, E. R.; Leigh, D. A.; Zerbetto, F. Angew. Chem., Int. Ed. 2007, 46, 72-191
58. Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302-1315
59. Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952-3015
60. Wu, P.; Fokin, V. V. Aldrichim. Acta 2007, 40, 7-17
61. Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021
62. Walsh, J. C.; Kolb, H. C. Chimia 2010, 64, 29-33
63. Waengler, C.; Schirrmacher, R.; Bartenstein, P.; Waengler, B. Curr. Med. Chem. 2010, 17, 1092-1116
64. Johnson, J. A.; Finn, M. G.; Koberstein, J. T.; Turro, N. J. Macromol. Rapid Commun. 2008, 29, 1052-1072
65. Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262
66. Aprahamian, I.; Miljanic, O. S.; Dichtel, W. R.; Isoda, K.; Yasuda, T.; Kato, T.; Stoddart, J. F. Bull. Chem. Soc. Jpn. 2007, 80, 1856-1869
67. Kolb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137
68. Hua, Y.; Flood, A. H. Chem. Soc. Rev. 2010, 39, 1262-1271
69. Holub, J. M.; Kirshenbaum, K. Chem. Soc. Rev. 2010, 39, 1325-1337
70. Haenni, K. D.; Leigh, D. A. Chem. Soc. Rev. 2010, 39, 1240-1251
71. Golas, P. L.; Matyjaszewski, K. Chem. Soc. Rev. 2010, 39, 1338-1354
72. El-Sagheer, A. H.; Brown, T. Chem. Soc. Rev. 2010, 39, 1388-1405
73. Aragao-Leoneti, V.; Campo, V. L.; Gomes, A. S.; Field, R. A.; Carvalho, I. Tetrahedron 2010, 66, 9475-9492
74. Struthers, H.; Mindt, T. L.; Schibli, R. Dalton Trans. 2010, 39, 675-696
75. Bai, S.-Q.; Young, D. J.; Hor, T. S. A. Chem. Asian J. 2011, 6, 292-304
76. Nakamura, T.; Terashima, T.; Ogata, K.; Fukuzawa, S.-i. Org. Lett. 2011, 13, 620-623
77. Poulain, A.; Canseco-Gonzalez, D.; Hynes-Roche, R.; Muller-Bunz, H.; Schuster, O.; Stoeckli-Evans, H.; Neels, A.; Albrecht, M. Organometallics 2011, 30, 1021-1029
78. Nakamura, T.; Ogata, K.; Fukuzawa, S.-i. Chem. Lett. 2010, 39, 920-922
79. Partyka, D. V.; Gao, L.; Teets, T. S.; Updegraff, J. B.; Deligonul, N.; Gray, T. G. Organometallics 2009, 28, 6171-6182
80. Partyka, D. V.; Updegraff, J. B., III; Zeller, M.; Hunter, A. D.; Gray, T. G. Organometallics 2007, 26, 183-186
81. Mathew, P.; Neels, A.; Albrecht, M. J. Am. Chem. Soc. 2008, 130, 13534-13535
82. Manbeck, G. F.; Brennessel, W. W.; Eisenberg, R. Inorg. Chem. 2011, 50, 3431-3441
83. Fleischel, O.; Wu, N.; Petitjean, A. Chem. Commun. 2010, 46, 8454-8456
84. Manbeck, G. F.; Brennessel, W. W.; Evans, C. M.; Eisenberg, R. Inorg. Chem. 2010, 49, 2834-2843
85. Urankar, D.; Pevec, A.; Turel, I.; Kosmrlj, J. Cryst. Growth Des. 2010, 10, 4920-4927
86. Chevry, A.; Teyssot, M.-L.; Maisonial, A.; Lemoine, P.; Viossat, B.; Traikia, M.; Aitken, D. J.; Alves, G.; Morel, L.; Nauton, L.; Gautier, A. Eur. J. Inorg. Chem. 2010, 3513-3519
87. Warsink, S.; Drost, R. M.; Lutz, M.; Spek, A. L.; Elsevier, C. J. Organometallics 2010, 29, 3109-3116
88. Fu, Y.; Liu, Y.; Zhong, C.; Li, H.; Chen, X.-G.; Qin, J.-G. Wuji Huaxue Xuebao 2010, 26, 1133-1140
89. Fu, Y.; Liu, Y.; Fu, X.; Zou, L.; Li, H.; Li, M.; Chen, X.; Qin, J. Chin. J. Chem. 2010, 28, 2226-2232
90. Kuang, G.-C.; Michaels, H. A.; Simmons, J. T.; Clark, R. J.; Zhu, L. J. Org. Chem. 2010, 75, 6540-6548
91. Brotherton, W. S.; Michaels, H. A.; Simmons, J. T.; Clark, R. J.; Dalal, N. S.; Zhu, L. Org. Lett. 2009, 11, 4954-4957
92. Felici, M.; Contreras-Carballada, P.; Vida, Y.; Smits, J. M. M.; Nolte, R. J. M.; De Cola, L.; Williams, R. M.; Feiters, M. C. Chem.-Eur. J. 2009, 15, 13124-13134
93. Beyer, B.; Ulbricht, C.; Escudero, D.; Friebe, C.; Winter, A.; Gonzalez, L.; Schubert, U. S. Organometallics 2009, 28, 5478-5488
94. Happ, B.; Escudero, D.; Hager, M. D.; Friebe, C.; Winter, A.; Gorls, H.; Altuntas, E.; Gonzalez, L.; Schubert, U. S. J. Org. Chem. 2010, 75, 4025-4038
95. Happ, B.; Friebe, C.; Winter, A.; Hager, M. D.; Hoogenboom, R.; Schubert, U. S. Chem.-Asian J. 2009, 4, 154-163
96. Maisonial, A.; Serafin, P.; Traikia, M.; Debiton, E.; Thery, V.; Aitken, D. J.; Lemoine, P.; Viossat, B.; Gautier, A. Eur. J. Inorg. Chem. 2008, 298-305
97. Richardson, C.; Fitchett, C. M.; Keene, F. R.; Steel, P. J. Dalton Trans. 2008, 2534-2537
98. Fletcher, J. T.; Bumgarner, B. J.; Engels, N. D.; Skoglund, D. A. Organometallics 2008, 27, 5430-5433
99. Yang, W.-W.; Wang, L.; Zhong, Y.-W.; Yao, J. Organometallics 2011, 30, 2236-2240
100. Brotherton, W. S.; Guha, P. M.; Phan, H.; Clark, R. J.; Shatruk, M.; Zhu, L. Dalton Trans. 2011, 40, 3655-3665
101. Danielraj, P.; Varghese, B.; Sankararaman, S. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2010, C66, m366-m370
102. Gu, S.; Xu, H.; Zhang, N.; Chen, W. Chem.-Asian J. 2010, 5, 1677-1686
103. Zhang, C.; Shen, X.; Sakai, R.; Gottschaldt, M.; Schubert, U. S.; Hirohara, S.; Tanihara, M.; Yano, S.; Obata, M.; Xiao, N.; Satoh, T.; Kakuchi, T. J. Polym. Sci., Part A: Polym. Chem. 2011, 49, 746-753
104. Ostermeier, M.; Berlin, M.-A.; Meudtner, R. M.; Demeshko, S.; Meyer, F.; Limberg, C.; Hecht, S. Chem.-Eur. J. 2010, 16, 10202-10213
105. Meudtner, R. M.; Ostermeier, M.; Goddard, R.; Limberg, C.; Hecht, S. Chem.-Eur. J. 2007, 13, 9834-9840
106. Schulze, B.; Friebe, C.; Hager, M. D.; Winter, A.; Hoogenboom, R.; Goerls, H.; Schubert, U. S. Dalton Trans. 2009, 787-794
107. Schuster, E. M.; Botoshansky, M.; Gandelman, M. Angew. Chem., Int. Ed. 2008, 47, 4555-4558
108. Li, Y.; Huffman, J. C.; Flood, A. H. Chem. Commun. 2007, 2692-2694
109. Schuster, E. M.; Nisnevich, G.; Botoshansky, M.; Gandelman, M. Organometallics 2009, 28, 5025-5031
110. Schuster, E. M.; Botoshansky, M.; Gandelman, M. Organometallics 2009, 28, 7001-7005
111. Garcia, L.; Maisonneuve, S. p.; Xie, J.; Guillot, R. g.; Dorlet, P.; Rivière, E.; Desmadril, M.; Lambert, F. o.; Policar, C. Inorg. Chem. 2010, 49, 7282-7288
112. Najar, A. M.; Tidmarsh, I. S.; Ward, M. D. CrystEngComm 2010, 12, 3642-3650
113. Hao, E.; Wang, Z.; Jiao, L.; Wang, S. Dalton Trans. 2010, 39, 2660-2666
114. Tamanini, E.; Flavin, K.; Motevalli, M.; Piperno, S.; Gheber, L. A.; Todd, M. H.; Watkinson, M. Inorg. Chem. 2010, 49, 3789-3800
115. Chandrasekhar, N.; Chandrasekar, R. J. Org. Chem. 2010, 75, 4852-4855
116. Bai, S.-Q.; Leelasubcharoen, S.-Y.; Chen, X.; Koh, L.-L.; Zuo, J.-L.; Hor, T. S. A. Cryst. Growth Des. 2010, 10, 1715-1720
117. Bai, S.-Q.; Kwang, J. Y.; Koh, L. L.; Young, D. J.; Hor, T. S. A. Dalton Trans. 2010, 39, 2631-2636
118. Kilpin, K. J.; Paul, U. S. D.; Lee, A.-L.; Crowley, J. D. Chem. Commun. 2011, 47, 328-330
119. Gower, M. L.; Crowley, J. D. Dalton Trans. 2010, 39, 2371-2378
120. Crowley, J. D.; Gavey, E. L. Dalton Trans. 2010, 39, 4035-4037
121. Kilpin, K. J.; Crowley, J. D. Polyhedron 2010, 29, 3111-3117
122. Crowley, J. D.; Bandeen, P. H.; Hanton, L. R. Polyhedron 2010, 29, 70-83
123. Crowley, J. D.; Bandeen, P. H. Dalton Trans 2010, 39, 612-623
124. Isolated azides have been used in the CuAAC "click" reaction to generate functionalized ligands, for examples see refs 17-25.
125. Camponovo, J.; Ruiz, J.; Cloutet, E.; Astruc, D. Chem.-Eur. J. 2009, 15, 2990-3002
126. Koester, S. D.; Dittrich, J.; Gasser, G.; Huesken, N.; Henao Castaneda, I. C.; Jios, J. L.; Della Vedova, C. O.; Metzler-Nolte, N. Organometallics 2008, 27, 6326-6332
127. Badeche, S.; Daran, J.-C.; Ruiz, J.; Astruc, D. Inorg. Chem. 2008, 47, 4903-4908
128. Ornelas, C.; Ruiz Aranzaes, J.; Cloutet, E.; Alves, S.; Astruc, D. Angew. Chem., Int. Ed. 2007, 46, 872-877
129. Michaels, H. A.; Murphy, C. S.; Clark, R. J.; Davidson, M. W.; Zhu, L. Inorg. Chem. 2010, 49, 4278-4287
130. Maity, D.; Govindaraju, T. Chem. Commun. 2010, 46, 4499-4501
131. Maity, D.; Govindaraju, T. Inorg. Chem. 2010, 49, 7229-7231
132. Xie, F.; Sivakumar, K.; Zeng, Q.; Bruckman, M. A.; Hodges, B.; Wang, Q. Tetrahedron 2008, 64, 2906-2914
133. Varazo, K.; Xie, F.; Gulledge, D.; Wang, Q. Tetrahedron Lett. 2008, 49, 5293-5296
134. Huang, S.; Clark, R. J.; Zhu, L. Org. Lett. 2007, 9, 4999-5002
135. Chang, K.-C.; Su, I.-H.; Senthilvelan, A.; Chung, W.-S. Org. Lett. 2007, 9, 3363-3366
136. Park, S. Y.; Yoon, J. H.; Hong, C. S.; Souane, R.; Kim, J. S.; Matthews, S. E.; Vicens, J. J. Org. Chem. 2008, 73, 8212-8218
137. Seridi, A.; Wolff, M.; Boulay, A.; Saffon, N.; Coulais, Y.; Picard, C.; Machura, B.; Benoist, E. Inorg. Chem. Commun. 2011, 14, 238-242
138. Benoist, E.; Coulais, Y.; Almant, M.; Kovensky, J.; Moreau, V.; Lesur, D.; Artigau, M.; Picard, C.; Galaup, C.; Gouin, S. G. Carbohydr. Res. 2011, 346, 26-34
139. Kim, E.-M.; Joung, M.-H.; Lee, C.-M.; Jeong, H.-J.; Lim, S. T.; Sohn, M.-H.; Kim, D. W. Bioorg. Med. Chem. Lett. 2010, 20, 4240-4243
140. Mindt, T. L.; Struthers, H.; Spingler, B.; Brans, L.; Tourwe, D.; Garcia-Garayoa, E.; Schibli, R. ChemMedChem 2010, 5, 2026-2038
141. Mindt, T. L.; Schweinsberg, C.; Brans, L.; Hagenbach, A.; Abram, U.; Tourwe, D.; Garcia-Garayoa, E.; Schibli, R. ChemMedChem 2009, 4, 529-539
142. Mindt, T. L.; Muller, C.; Stuker, F.; Salazar, J.-F.; Hohn, A.; Mueggler, T.; Rudin, M.; Schibli, R. Bioconjugate Chem. 2009, 20, 1940-1949
143. Struthers, H.; Spingler, B.; Mindt, T. L.; Schibli, R. Chem.-Eur. J. 2008, 14, 6173-6183
144. Ross, T. L.; Honer, M.; Lam, P. Y. H.; Mindt, T. L.; Groehn, V.; Schibli, R.; Schubiger, P. A.; Ametamey, S. M. Bioconjugate Chem. 2008, 19, 2462-2470
145. Mindt, T. L.; Mueller, C.; Melis, M.; de Jong, M.; Schibli, R. Bioconjugate Chem. 2008, 19, 1689-1695
146. Mindt, T. L.; Struthers, H.; Brans, L.; Anguelov, T.; Schweinsberg, C.; Maes, V.; Tourwe, D.; Schibli, R. J. Am. Chem. Soc. 2006, 128, 15096-15097
147. Felici, M.; Contreras-Carballada, P.; Smits, J. M. M.; Nolte, R. J. M.; Williams, R. M.; De Cola, L.; Feiters, M. C. Molecules 2010, 15, 2039-2059
148. Obata, M.; Kitamura, A.; Mori, A.; Kameyama, C.; Czaplewska, J. A.; Tanaka, R.; Kinoshita, I.; Kusumoto, T.; Hashimoto, H.; Harada, M.; Mikata, Y.; Funabiki, T.; Yano, S. Dalton Trans. 2008, 3292-3300
149. Feldman, A. K.; Colasson, B.; Fokin, V. V. Org. Lett. 2004, 6, 3897-3899
150. Li, Y.; Flood, A. H. Angew. Chem., Int. Ed. 2008, 47, 2649-2652
151. Li, Y.; Flood, A. H. J. Am. Chem. Soc. 2008, 130, 12111-12122
152. Li, Y.; Pink, M.; Karty, J. A.; Flood, A. H. J. Am. Chem. Soc. 2008, 130, 17293-17295
153. Andersen, J.; Bolvig, S.; Liang, X. Synlett 2005, 2941-2947
154. Andersen, J.; Madsen, U.; Bjorkling, F.; Liang, X. Synlett 2005, 2209-2213
155. Grimes, K. D.; Gupte, A.; Aldrich, C. C. Synthesis 2010, 1441-1448
156. Tao, C.-Z.; Cui, X.; Li, J.; Liu, A.-X.; Liu, L.; Guo, Q.-X. Tetrahedron Lett. 2007, 48, 3525-3529
157. Boulay, A.; Seridi, A.; Zedde, C.; Ladeira, S.; Picard, C.; Maron, L.; Benoist, E. Eur. J. Inorg. Chem. 2010, 5058-5062
158. Happ, B.; Hoogenboom, R.; Winter, A.; Hager, M. D.; Baumann, S. O.; Kickelbick, G.; Schubert, U. S. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o1146
159. Crowley, J. D.; Bandeen, P. H.; Hanton, L. R. Acta Crystallogr., Sect. E: Struct. Rep. Online 2009, E65, o999-o1000
160. Schweinfurth, D.; Hardcastle, K. I.; Bunz, U. H. F. Chem. Commun. 2008, 2203-2205
161. Lyons, T. W.; Sanford, M. S. Chem. Rev. 2010, 110, 1147-1169
162. Xu, L.-M.; Li, B.-J.; Yang, Z.; Shi, Z.-J. Chem. Soc. Rev. 2010, 39, 712-733
163. Wu, X.-F.; Anbarasan, P.; Neumann, H.; Beller, M. Angew. Chem., Int. Ed. 2010, 49, 9047-9050
164. Valente, C.; Belowich, M. E.; Hadei, N.; Organ, M. G. Eur. J. Org. Chem. 2010, 4343-4354
165. Sivaramakrishna, A.; Clayton, H. S.; Mogorosi, M. M.; Moss, J. R. Coord. Chem. Rev. 2010, 254, 2904-2932
166. Sehnal, P.; Taylor, R. J. K.; Fairlamb, I. J. S. Chem. Rev. 2010, 110, 824-889
167. Grigg, R.; Mutton, S. P. Tetrahedron 2010, 66, 5515-5548
168. Moreno, I.; SanMartin, R.; Ines, B.; Herrero, M. T.; Dominguez, E. Curr. Org. Chem. 2009, 13, 878-895
169. McGlacken, G. P.; Fairlamb, I. J. S. Eur. J. Org. Chem. 2009, 4011-4029
170. Gligorich, K. M.; Sigman, M. S. Chem. Commun. 2009, 3854-3867
171. Chen, X.; Engle, K. M.; Wang, D.-H.; Yu, J.-Q. Angew. Chem., Int. Ed. 2009, 48, 5094-5115
172. Bianchini, C.; Shen, P. K. Chem. Rev. 2009, 109, 4183-4206
173. Anaya de Parrodi, C.; Walsh, P. J. Angew. Chem., Int. Ed. 2009, 48, 4679-4682
174. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874-922
175. Cornell, C. N.; Sigman, M. S. Inorg. Chem. 2007, 46, 1903-1909
176. Gao, E.; Liu, C.; Zhu, M.; Lin, H.; Wu, Q.; Liu, L. Anti-Cancer Agents Med. Chem. 2009, 9, 356-368
177. Garoufis, A.; Hadjikakou, S. K.; Hadjiliadis, N. Coord. Chem. Rev. 2009, 253, 1384-1397
178. Abu-Surrah, A. S.; Al-Sa'doni, H. H.; Abdalla, M. Y. Cancer Therapy 2008, 6, 1-10
179. Yoshizawa, M.; Fujita, M. Bull. Chem. Soc. Jpn. 2010, 83, 609-618
180. Yoshizawa, M.; Klosterman, J. K.; Fujita, M. Angew. Chem., Int. Ed. 2009, 48, 3418-3438
181. Klosterman, J. K.; Yamauchi, Y.; Fujita, M. Chem. Soc. Rev. 2009, 38, 1714-1725
182. Crowley, J. D.; Bosnich, B. Eur. J. Inorg. Chem. 2005, 2015-2025
183. When we began this project there had been no reports on the coordination chemistry of these 2-pyridyl-1,2,3-triazole ligands with palladium(II). However, during the course of our work two groups have published in this area, see, refs 36 and 37. Additionally, we have reported some preliminary studies on Pd(II) dichloride complexes, see ref 16.
184. Schweinfurth, D.; Pattacini, R.; Strobel, S.; Sarkar, B. Dalton Trans. 2009, 9291-9297
185. Schweinfurth, D.; Strobel, S.; Sarkar, B., Inorg. Chim. Acta 2011, DOI: 10.1016/j.ica.2011.02.085.
186. Urankar, D.; Pinter, B.; Pevec, A.; De Proft, F.; Turel, I.; Kosmrlj, J. Inorg. Chem. 2010, 49, 4820-4829
187. Geary, W. J. Coord. Chem. Rev. 1971, 7, 81-122
188. Bastero, A.; Font, D.; Pericas, M. A. J. Org. Chem. 2007, 72, 2460-2468
189. A similar hydrogen bonding interaction has been observed in 2-pyridyl pyrazolates complexes of Pt(II), see
190. Wang, K.-W.; Chen, J.-L.; Cheng, Y.-M.; Chung, M.-W.; Hsieh, C.-C.; Lee, G.-H.; Chou, P.-T.; Chen, K.; Chi, Y. Inorg. Chem. 2010, 49, 1372-1383
191. Chang, S.-Y.; Kavitha, J.; Hung, J.-Y.; Chi, Y.; Cheng, Y.-M.; Li, E. Y.; Chou, P.-T.; Lee, G.-H.; Carty, A. J. Inorg. Chem. 2007, 46, 7064-7074
192. Chang, S.-Y.; Kavitha, J.; Li, S.-W.; Hsu, C.-S.; Chi, Y.; Yeh, Y.-S.; Chou, P.-T.; Lee, G.-H.; Carty, A. J.; Tao, Y.-T.; Chien, C.-H. Inorg. Chem. 2006, 45, 137-146
193. Liao, C.-T.; Chen, H.-H.; Hsu, H.-F.; Poloek, A.; Yeh, H.-H.; Chi, Y.; Wang, K.-W.; Lai, C.-H.; Lee, G.-H.; Shih, C.-W.; Chou, P.-T. Chem.-Eur. J. 2011, 17, 546-556
194. Ward, M. D.; Fleming, J. S.; Psillakis, E.; Jeffery, J. C.; McCleverty, J. A. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1998, C54, 609-612
195. During the course of this work, a report on the crystal structure of 4c appeared in the literature, see ref 37. We have also independently determined the same structure; however, a discussion of this compound will be limited to the Supporting Information.
196. Verschoor-Kirss, M.; Kreisz, J.; Feighery, W.; Reiff, W. M.; Frommen, C. M.; Kirss, R. U. J. Organomet. Chem. 2009, 694, 3262-3269
197. Altomare, A.; Burla, M. C.; Camalli, M.; Cascarano, G. L.; Giacovazzo, C.; Guagliardi, A.; Moliterni, A. G. G.; Polidori, G.; Spagna, R. J. Appl. Crystallogr. 1999, 32, 115-119
198. Sheldrick, G. M.; Schneider, T. R. Methods Enzymol. 1997, 277, 319-343
199. Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
200. Bratsos, I.; Urankar, D.; Zangrando, E.; Genova-Kalou, P.; Kosmrlj, J.; Alessio, E.; Turel, I. Dalton Trans. 2011, 40, 5188-5199
201. Urankar, D.; Pevec, A.; Kosmrlj, J. Eur. J. Inorg. Chem. 2011, 1921-1929
202. Amadio, E.; Bertoldini, M.; Scrivanti, A.; Chessa, G.; Beghetto, V.; Matteoli, U.; Bertani, R.; Dolmella, A. Inorg. Chim. Acta 2011, 370, 388-393