Stable N-heterocyclic carbene (NHC)-palladium(0) complexes as active catalysts for olefin cyclopropanation reactions with ethyl diazoacetate

Chemistry - A European Journal

Volumn 17, Issue 52, 2011, Pages 14885-14895

  Martín, Carmen ^a   Molina, Francisco ^a   Alvarez, Eleuterio ^b   Belderrain, Tomás R ^a  

^a UNIVERSITY OF HUELVA   (Spain)

^b INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

cyclopropanation; diazo compounds; homogeneous catalysis; palladium

Indexed keywords

ACTIVE CATALYST; CARBENES; CATALYSE; CATALYST PRECURSORS; CATALYTIC SPECIES; CATALYTIC SYSTEM; CYCLOPROPANATION; DIAZO COMPOUNDS; ETHYL DIAZOACETATE; HOMOGENEOUS CATALYSIS; MECHANISTIC STUDIES; N-HETEROCYCLIC CARBENE LIGANDS; N-HETEROCYCLIC CARBENES; OLEFIN CYCLOPROPANATION;

CARBON INORGANIC COMPOUNDS; CATALYSTS; LIGANDS; OLEFINS; ORGANIC COMPOUNDS; PALLADIUM; PROPANE; REACTION KINETICS; STYRENE;

PALLADIUM COMPOUNDS;

CARBENE; DIAZOACETIC ACID ETHYL ESTER; DIAZONIUM COMPOUND; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; METHANE; ORGANOMETALLIC COMPOUND; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DIAZONIUM COMPOUNDS; HETEROCYCLIC COMPOUNDS; LIGANDS; METHANE; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM;

EID: 83755172284     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102900     Document Type: Article

References (185)

1. H. Pellissier, Tetrahedron 2008, 64, 7041-7095
2. A. de Meijere, Small Ring Compounds in Organic Synthesis VI, Vol. 207: Topics in Current Chemistry, Springer, Berlin, 2000.
3. M. P. Doyle, A. McKervey, T. Ye, Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides, John Wiley & Sons, New York, 1998
4. M. P. Doyle, Chem. Rev. 1986, 86, 919-939
5. H. Lebel, J.-F. Marcoux, C. Molinaro, A. B. Charette, Chem. Rev. 2003, 103, 977-1050
6. H. M. L. Davies, R. E. J. Beckwith, Chem. Rev. 2003, 103, 2861-2903
7. W. Kirmse, Angew. Chem. 2003, 115, 1120-1125
8. Angew. Chem. Int. Ed. 2003, 42, 1088-1093
9. A. Caballero, A. Prieto, M. M. Díaz-Requejo, P. J. Pérez, Eur. J. Inorg. Chem. 2009, 1137-1144
10. Z. Zhang, J. Wang, Tetrahedron 2008, 64, 6577-6605
11. H. M. L. Davies, S. J. Hedley, Chem. Soc. Rev. 2007, 36, 1109-1119.
12. A. Ghanem, M. G. Gardiner, R. M. Williamson, P. Müller, Chem. Eur. J. 2010, 16, 3291-3295
13. T. Nishimura, Y. Maeda, T. Hayashi, Angew. Chem. 2010, 122, 7482-7485
14. Angew. Chem. Int. Ed. 2010, 49, 7324-7327
15. T. M. Gregg, R. F. Algera, J. R. Frost, F. Hassan, R. J. Stewart, Tetrahedron Lett. 2010, 51, 6429-6432
16. I. Suárez del Villar, A. Gradillas, J. Pérez-Castells, Eur. J. Org. Chem. 2010, 5850-5862
17. D. Marcoux, V. N. G. Lindsay, A. B. Charette, Chem. Commun. 2010, 46, 910-912
18. V. N. G. Lindsay, W. Lin, A. B. Charette, J. Am. Chem. Soc. 2009, 131, 16383-16385
19. D. L. Ventura, Z. Li, M. G. Coleman, H. M. L. Davies, Tetrahedron 2009, 65, 3052-3061
20. T. Lu, Z. L. Song, R. P. Hsung, Org. Lett. 2008, 10, 541-544
21. F. González-Bobes, M. D. B. Fenster, S. Kiau, L. Kolla, S. Kolotuchin, M. Soumeillanta, Adv. Synth. Catal. 2008, 350, 813-816
22. S. Muthusamy, P. Srinivasan, Tetrahedron Lett. 2006, 47, 6297-6300
23. M. P. Doyle, J. Org. Chem. 2006, 71, 9253-9260
24. J. A. S. Howell, Dalton Trans. 2007, 1104-1114
25. T. Niino, M. Toganoh, B. Andrioletti, H. Furuta, Chem. Commun. 2006, 4335-4337
26. F. Estevan, J. Lloret, M. Sanaú, M. A. Úbeda, Organometallics 2006, 25, 4977-4984
27. M. P. Doyle, T. M. Weathers, Jr., Y. Wanga, Adv. Synth. Catal. 2006, 348, 2403-2409
28. W. Lin, A. B. Charette, Adv. Synth. Catal. 2005, 347, 1547-1552
29. F. Estevan, P. Lahuerta, J. Lloret, M. Sanaú, M. A. Úbeda, J. Vila, Chem. Commun. 2004, 2408-2409
30. J. S. Yadav, B. V. S. Reddy, P. N. Reddy, Adv. Synth. Catal. 2004, 346, 53-56.
31. Y. Zhu, C. Zhai, L. Yang, W. Hu, Chem. Commun. 2010, 46, 2865-2867
32. J. Wassenaar, M. A. Siegler, A. L. Spek, B. de Bruin, J. N. H. Reek, J. I. van der Vlugt, Inorg. Chem. 2010, 49, 6495-6508
33. A. Corma, M. Iglesias, F. X. Llabrés i Xamena, F. Sánchez, Chem. Eur. J. 2010, 16, 9789-9795
34. R. Ahuja, A. G. Samuelson, J. Organomet. Chem. 2009, 694, 1153-1160
35. C. Özen, F. Aylin, S. Konuklar, N. S. Tuhzuhn, Organometallics 2009, 28, 4964-4973
36. I. V. Shishkov, F. Rominger, P. Hofmann, Organometallics 2009, 28, 1049-1059
37. S. T. Handy, A. Ivanow, Inorg. Chim. Acta 2009, 362, 4468-4471
38. N. P. Mankad, J. C. Peter, Chem. Commun. 2008, 1061-1063
39. P. Hofmann, I. V. Shishkov, F. Rominger, Inorg. Chem. 2008, 47, 11755-11762
40. J.-M. Fraile, J.-I. García, A. Gissibl, J.-A. Mayoral, E. Pires, O. Reiser, M. Roldán, I. Villalba, Chem. Eur. J. 2007, 13, 8830-8839
41. G. Lesma, C. Cattenati, T. Pilati, A. Sacchettia, A. Silvani, Tetrahedron: Asymmetry 2007, 18, 659-663
42. R. L. Safiullin, V. A. Dokichev, L. R. Yakupova, R. M. Sultanova, S. L. Khursan, R. N. Zaripov, Y. V. Tomilov, Kinetics and Catalysis 2008, 49, 43-51
43. C. Ricardo, T. Pintauer, J. Organomet. Chem. 2007, 692, 5165-5172
44. K. Suenobu, M. Itagaki, N. Eiichi, J. Am. Chem. Soc. 2004, 126, 7271-7280
45. D. Xuliang, T. H. Warren, J. Am. Chem. Soc. 2004, 126, 10085-10094
46. A. Caballero, M. M. Díaz-Requejo, S. Trofimenko, T. R. Belderrain, P. J. Pérez, J. Org. Chem. 2005, 70, 6101-6104
47. M. R. Fructos, T. R. Belderrain, M. C. Nicasio, S. P. Nolan, H. Kaur, M. M. Díaz-Requejo, P. J. Pérez, J. Am. Chem. Soc. 2004, 126, 10846-10847
48. M. M. Díaz-Requejo, T. R. Belderrain, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2001, 123, 3167-3168
49. M. M. Díaz-Requejo, A. Caballero, T. R. Belderrain, M. C. Nicasio, S. Trofimenko, P. J. Pérez, J. Am. Chem. Soc. 2002, 124, 978-983.
50. K. B. Fields, J. T. Engle, S. Sripothongnak, C. Kim, X. P. Zhang, C. J. Ziegler, Chem. Commun. 2011, 47, 749-751
51. S. F. Zhu, X. Xu, J. A. Perman, X. P. Zhang, J. Am. Chem. Soc. 2010, 132, 12796-12799
52. W. I. Dzik, X. Xu, X. P. Zhang, J. N. H. Reek, B. de Bruin, J. Am. Chem. Soc. 2010, 132, 10891-10902
53. N. S. Youssef, E. A. El-Zahany, B. N. Barsoum, A. M. A. El-Seidy, Transition Metal Chemistry 2009, 34, 905-914
54. J. V. Ruppel, T. J. Gauthier, N. L. Snyder, J. A. Perman, X. P. Zhang, Org. Lett. 2009, 11, 2273-2276
55. C.-T. Yeung, K.-C. Sham, W.-S. Lee, W.-T. Wong, W.-Y. Wong, H.-L. Kwong, Inorg. Chim. Acta 2009, 362, 3267-3273
56. M. P. Doyle, Angew. Chem. 2009, 121, 864-866
57. Angew. Chem. Int. Ed. 2009, 48, 850-852
58. S. Fantauzzi, E. Gallo, E. Rose, N. Raoul, A. Caselli, S. Issa, F. Ragaini, S. Cenini, Organometallics 2008, 27, 6143-6151
59. S. Zhu, J. A. Perman, X. P. Zhang, Angew. Chem. 2008, 120, 8588-8591; Angew. Chem. Int. Ed. 2008, 47, 8460- 8463
60. Angew. Chem. Int. Ed. 2008, 47, 8460-8463
61. S. F. Zhu, J. V. Ruppel, H. J. Lu, L. Wojtas, X. P. Zhang, J. Am. Chem. Soc. 2008, 130, 5042-5043
62. Y. Chen, J. V. Ruppel, X. P. Zhang, J. Am. Chem. Soc. 2007, 129, 12074-12075
63. H. Shitama, T. Katsuki, Chem. Eur. J. 2007, 13, 4849-4858
64. Y. Chen, X. P. Zhang, J. Org. Chem. 2007, 72, 5931-5934
65. Y. Chen, X. P. Zhang, Synthesis 2006, 1679
66. T. Uchida, T. Katsuki, Synthesis 2006, 1715-1723
67. A. Caselli, E. Gallo, F. Ragaini, F. Ricatto, G. Abbiati, S. Cenini, Inorg. Chim. Acta 2006, 359, 2924-2932
68. Y. Chen, G.-Y. Gao, X. P. Zhang, Tetrahedron Lett. 2005, 46, 4965-4969
69. Y. Chen, X. P. Zhang, J. Org. Chem. 2004, 69, 2431-2435
70. Y. Chen, K. B. Fields, X. P. Zhang, J. Am. Chem. Soc. 2004, 126, 14718-14719
71. I. Iwakura, T. Ikeno, T. Yamada, Org. Lett. 2004, 6, 949-952.
72. B. Morandi, E. M. Carreira, Angew. Chem. 2010, 122, 950
73. Angew. Chem. Int. Ed. 2010, 49, 938-941
74. P. Le Maux, I. Nicolas, S. Chevance, G. Simonneaux, Tetrahedron 2010, 66, 4462-4468
75. S. R. Wang, C.-Y. Zhu, X.-L Sun, Y. Tang, J. Am. Chem. Soc. 2009, 131, 4192-4193
76. I. Nicolas, T. Roisnel, P. Le Maux, G. Simonneaux, Tetrahedron Lett. 2009, 50, 5149-5151
77. T. S. Lai, F. Y Chan, P. K. So, D. L. Ma, K. Y Wong, C. M. Che, Dalton Trans. 2006, 4845-4851
78. Q. Wang, F. H. Försterling, M. M. Hossain, J. Organomet. Chem. 2005, 690, 6238-6246
79. S. K. Edulji, S. T. Nguyen, Organometallics 2003, 22, 3374-3381
80. P. Tagliatesta, A. Pastorini, J. Mol. Catal. A: Chem. 2003, 198, 57-61.
81. A. M. Abu-Elfotoh, K. Phomkeona, K. Shibatomi, S. Iwasa, Angew. Chem. 2010, 122, 8617-8621
82. Angew. Chem. Int. Ed. 2010, 49, 8439-8443
83. Z. J. Xu, R. Fang, C. Zhao, J. S. Huang, G. Y. Li, N. Zhu, C. M. Che, J. Am. Chem. Soc. 2009, 131, 4405-4417
84. C. S. Gill, K. Venkatasubbaiah, C. W. Jones, Adv. Synth. Catal. 2009, 351, 1344-1354
85. I. Nicolas, P. Le Maux, G. Simonneaux, Tetrahedron Lett. 2008, 49, 2111-2113
86. R. P. Murelli, S. Catalan, M. P. Gannon, M. L. Snapper, Tetrahedron Lett. 2008, 49, 5714-5717
87. V. D. M. Hoang, P. A. N. Reddy, T. J. Kim, Tetrahedron Lett. 2007, 48, 8014-8017
88. J. Goux, P. Le Gendre, P. Richard, C. Moise, J. Organomet. Chem. 2006, 691, 3239-3244
89. D. Huber, P. G. A. Kumar, P. S. Pregosin, I. S. Mikhel, A. Mezzetti, Helv. Chim. Acta 2006, 89, 1696-1715
90. B. G. Kim, M. L. Snapper, J. Am. Chem. Soc. 2006, 128, 52-53
91. G. Y. Li, J. Zhang, P. W. H. Chan, Z. J. Xu, N. Y. Zhu, C. M. Che, Organometallics 2006, 25, 1676-1688
92. A. Tudose, A. Demonceau, L. Delaude, J. Organomet. Chem. 2006, 691, 5356-5365
93. K. Villeneuve, W. Tam, Organometallics 2006, 25, 843-848
94. A. Cornejo, J. M. Fraile, J. I. Garcia, M. J. Gil, V. Martinez-Merino, J. A. Mayoral, L. Salvatella, Angew. Chem. 2005, 117, 462-465
95. Angew. Chem. Int. Ed. 2005, 44, 458-461
96. J. Goux, P. Le Gendre, P. Richard, C. Moise, J. Organomet. Chem. 2005, 690, 301-306
97. M. Lasa, P. Lopez, C. Cativiela, D. Carmona, L. A. Oro, J. Mol. Catal. A: Chem. 2005, 234, 129-135
98. J. A. Miller, B. A. Gross, M. A. Zhuravel, W. C. Jin, S. T. Nguyen, Angew. Chem. 2005, 117, 3953-3957
99. Angew. Chem. Int. Ed. 2005, 44, 3885-3889
100. T. Werle, L. Schaffler, G. C. Maas, J. Organomet. Chem. 2005, 690, 5562-5569
101. D. Huber, A. Mezzetti, Tetrahedron: Asymmetry 2004, 15, 2193-2197
102. K. Miki, K. Ohe, S. Uemura, Tetrahedron Lett. 2003, 44, 2019-2022
103. K. Miki, K. Ohe, S. Uemura, J. Org. Chem. 2003, 68, 8505-8513
104. C. Paul-Roth, F. De Montigny, G. Rehtore, G. Simonneaux, M. Gulea, S. A. Masson, J. Mol. Catal. A: Chem. 2003, 201, 79-91.
105. R. K. Armstrong, J. Org. Chem. 1966, 31, 618-620
106. R. A. Paulissen, J. Hubert, P. Teyssié, Tetrahedron Lett. 1972, 13, 1465-1468.
107. O. N. Shishilov, T. A. Stromnova, J. Campora, P. Palma, M. A. Cartes, L. M. Martinez-Prieto, Dalton Trans. 2009, 6626-6633
108. S. F. Chen, J. Ma, J. B. Wang, Tetrahedron Lett. 2008, 49, 6781-6783
109. M. A. Emerzian, W. Davenport, J. G. Song, J. Li, I. Erden, Adv. Synth. Catal. 2009, 351, 999-1004
110. G. Berthon-Gelloz, M. Marchant, B. F. Straub, I. E. Markõ, Chem. Eur. J. 2009, 15, 2923-2931
111. M. D. Khanova, R. M. Sultanova, R. R. Rafikov, I. P. Baykova, R. Z. Biglova, V. A. Dokichev, Y. V. Tomilov, Russ. Chem. Bull. 2008, 57, 617-621
112. M. D. Khanova, R. M. Sultanova, S. S. Zlotskii, V. A. Dokichev, Y. V. Tomilov, Russ. Chem. Bull. 2005, 54, 1003-1007
113. M. Lakshmi Kantam, Y. Haritha, N. Mahender Reddy, B. M. Choudary, F. Figueras, Catal. Lett. 2002, 83, 187-190
114. M. Dubs, H. Dieks, W. Gunther, M. Kotteritzsch, W. Poppitz, B. Schonecker, Tetahedron. Lett. 2002, 43, 2499-2503
115. S. I. Kozhushkov, D. S. Yufit, R. Boese, D. Blaser, P. R. Schreiner, A. de Meijere, Eur. J. Org. Chem. 2005, 1409-1415
116. E. V. Guseva, N. V. Volchkov, Y. V. Tomilov, O. M. Nefedov, Eur. J. Org. Chem. 2004, 3136-3144
117. I. E. Markõ, T. Kumamoto, T. Girad, Adv. Synth. Catal. 2002, 344, 1063-1067.
118. Y. Zhang, J. Wang, Eur. J. Org. Chem. 2011, 1015-1026.
119. A. Nakamura, T. Koyama, S. Otsuka, Bull. Chem. Soc. Jpn. 1978, 51, 593-595
120. M. W. Majchrzak, A. Kotelko, J. B. Lambert, Synthesis-Stuttgart 1983, 469-470
121. A. J. Anciaux, A. J. Hubert, A. F. Noels, N. Petiniot, P. Teyssie, J. Org. Chem. 1980, 45, 695-702
122. K. J. Miller, J. H. Baag, M. M. Abu-Omar, Inorg. Chem. 1999, 38, 4510-4514.
123. M. M. Diaz-Requejo, P. J. Perez, Chem. Rev. 2008, 108, 3379-3394
124. P. de Fremont, E. D. Stevens, M. R. Fructos, M. M. Diaz-Requejo, P. J. Perez, S. P. Nolan, Chem. Commun. 2006, 2045-2047
125. M. R. Fructos, P. de Fremont, S. P. Nolan, M. M. Diaz-Requejo, P. J. Perez, Organometallics 2006, 25, 2237-2241
126. M. M. Diaz-Requejo, P. J. Perez, J. Organomet. Chem. 2005, 690, 24-25
127. M. R. Fructos, T. R. Belderrain, P. de Fremont, N. M. Scott, S. P. Nolan, M. M. Diaz-Requejo, P. J. Perez, Angew. Chem. 2005, 117, 5418-5422
128. Angew. Chem. Int. Ed. 2005, 44, 5284-5288.
129. E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. 2007, 119, 2824-2870
130. Angew. Chem. Int. Ed. 2007, 46, 2768-2813
131. S. Díez-González, N. Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676
132. M. Poyatos, J. A. Mata, E. Peris, Chem. Rev. 2009, 109, 3677-3707
133. N. Marion, S. P. Nolan, Acc. Chem. Res. 2008, 41, 1440-1449
134. S. Würtz, F. Glorius, Acc. Chem. Res. 2008, 41, 1523-1533
135. W. A. Herrmann, K. Öfele, D. V. Preysing, S. K. Schneider, J. Organomet. Chem. 2003, 687, 229-248
136. 3} complexes as catalysts, see
137. S. Fantasia, J. D. Egbert, V. Jurčík, C. S. J. Cazin, H. Jacobsen, L. Cavallo, D. M. Heinekey, S. P. Nolan, Angew. Chem. 2009, 121, 5284-5288
138. Angew. Chem. Int. Ed. 2009, 48, 5182-5186
139. O. Diebolt, V. Jurčík, P. Braunstein, L. Cavallo, S. P. Nolan, C. S. J. Cazin, Organometallics 2010, 29, 1443-1450
140. V. Jurčík, S. P. Nolan, C. S. J. Cazin, Chem. Eur. J. 2009, 15, 2509-2511.
141. 4) as the initiating system for polymerisation of ethyl diazoacetate, but no reaction with olefins was reported:, E. Ihara, Y. Ishiguro, N. Yoshida, T. Hiraren, T. Itoh, K. Inoue, Macromolecules 2009, 42, 8608-8610.
142. F. Bernardi, A. Bottoni, G. P. Miscione, Organometallics 2001, 20, 2751-2758
143. C. Rodríguez-García, A. Oliva, R. M. Ortuño, V. Branchadell, J. Am. Chem. Soc. 2001, 123, 6157-6163
144. C. Rodríguez-García, O. Gonzalez-Blanco, A. Oliva, R. M. Ortuño, V. Branchadell, Eur. J. Inorg. Chem. 2000, 1073-1078
145. B. F. Straub, J. Am. Chem. Soc. 2002, 124, 14195-14201.
146. K. Selvakumar, A. Zapf, A. Spannenberg, M. Beller, Chem. Eur. J. 2002, 8, 3901-3906
147. R. Jackstell, M. G. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028-1031
148. Angew. Chem. Int. Ed. 2002, 41, 986-989
149. R. Jackstell, S. Harkal, H. J. Jiao, A. Spannenberg, C. Borgmann, D. Rottger, F. Nierlich, M. Elliott, S. Niven, K. Cavell, O. Navarro, M. S. Viciu, S. P. Nolan, M. Beller, Chem. Eur. J. 2004, 10, 3891-3900
150. N. D. Clement, K. J. Cavell, L. Ooi, Organometallics 2006, 25, 4155-4165
151. P. Hauwert, G. Maestri, J. W. Sprengers, M. Catellani, C. J. Elsevier, Angew. Chem. 2008, 120, 3267-3270
152. Angew. Chem. Int. Ed. 2008, 47, 3223-3226
153. S. Warsink, I.-H. Chang, J. J. Weigand, P. Hauwert, J.-T. Chen, C. J. Elsevier, Organometallics 2010, 29, 4555-4561
154. L. Torrente-Murciano, A. Lapkin, D. J. Nielsen, I. Fallis, K. J. Cavell, Green Chem. 2010, 12, 866-869
155. J.-Y. Lee, P.-Y. Cheng, Y.-H. Tsai, G.-R. Lin, S.-P. Liu, M.-H. Sie, H. M. Lee, Organometallics 2010, 29, 3901-3911.
156. L. R. Titcomb, S. Caddick, F. G. N. Cloke, D. J. Wilson, D. McKerrecher, Chem. Commun. 2001, 1388-1389
157. C. W. K. Gstöttmayr, V. P. W. Böhm, E. Herdtweck, M. Grosche, W. A. Herrmann, Angew. Chem. 2002, 114, 1421-1423
158. Angew. Chem. Int. Ed. 2002, 41, 1363-1365.
159. S. Fantasia, S. P. Nolan, Chem. Eur. J. 2008, 14, 6987-6993.
160. See, for example, this article by R. Taube and co-workers in which a comparison of the metal-olefin bond in palladium and rhodium styrene complexes was made:, C. Hahn, A. Vitagliano, F. Giordano, R. Taube, Organometallics 1998, 17, 2060-2066.
161. B. V. Popp, J. L. Thorman, C. M. Morales, C. R. Landis, S. S. Stahl, J. Am. Chem. Soc. 2004, 126, 14832-14842.
162. It has been proposed that dissociation of MA from the [(IMes)Pd(MA)(alkyne)] complex affords a 16 electron species, allowing the subsequent coordination of a formate anion, see:, P. Hauwert, R. Boerleider, S. Warsink, J. J. Weigand, C. J. Elsevier, J. Am. Chem. Soc. 2010, 132, 16900-16910.
163. J. C. Cochran, K. Hagen, G. Paulen, Q. Shen, S. Tom, M. Traetteberg, C. Wells, J. Mol. Struct. 1997, 413-414, 313-326.
164. C. Hahn, J. Sieler, R. Taube, Chem. Ber. 1997, 130, 939-945.
165. K. Miki, O. Shiotani, Y. Kai, N. Kasai, H. Kanatani, H. Kurosawag, Organometallics 1983, 2, 585-593.
166. R. A. Wanat, D. B. Collum, Organometallics 1986, 5, 120-127.
167. F. M. Pedro, A. M. Santos, W. Baratta, F. E. Kühn, Organometallics 2007, 26, 302-309, and references therein
168. M. H. Kayser, D. L. Hooper, Can. J. Chem. 1990, 68, 2123-2128
169. M. H. Kayser, K. L. Hatt, D. L. Hooper, Can. J. Chem. 1991, 69, 1929-1939
170. P. Crews, J. Am. Chem. Soc. 1968, 90, 2961-2962
171. D. M. Crouse, A. T. Wehman, E. E. Schweizer, J. Chem Soc. Chem. Commun. 1968, 866-867.
172. 3-allyl)palladium complex with deprotonated isobutyronitrile. By passing carbon monoxide over solutions of the palladacycle, the reductive elimination took place and the corresponding cyclopropane and palladium(0) were formed:, H. M. R. Hoffmann, A. R. Otte, A. Wilde, S. Menzer, D. J. Williams, Angew. Chem. 1995, 107, 73-76
173. Angew. Chem. Int. Ed. Engl. 1995, 34, 100-102.
174. B. F. Straub, I. Gruber, F. Rominger, P. Hofmann, J. Organomet. Chem. 2003, 684, 124-143
175. T. Rasmussen, J. F. Jensen, N. Østergaard, D. Tanner, T. Ziegler, P.-O. Norrby, Chem. Eur. J. 2002, 8, 177-184.
176. A. J. Arduengo, R. Krafczyk, R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523-14534
177. R. Schmutzler, H. A. Craig, J. R. Goerlich, W. J. Marshall, M. Unverzagt, Tetrahedron 1999, 55, 14523-14534.
178. V. V. Grushin, C. Bensimon, H. Alper, Inorg. Chem. 1994, 33, 4804-4806.
179. P. J. Pérez, M. Brookhart, J. L Templeton, Organometallics 1993, 12, 261-262, and references therein
180. D.-J. Cho, S.-J. Jeon, H.-S. Kim, C.-S. Cho, S.-C. Shim, T.-J. Kim, Tetrahedron: Asymmetry 1999, 10, 3833-3848.
181. J. R. Wolf, C. G. Hamaker, J.-P. Djukic, T. Kodadek, L. K. Woo, J. Am. Chem. Soc. 1995, 117, 9194-9199.
182. APEX2, version 2.1, Bruker AXS Inc., Madison, 2004.
183. SAINT and SADABS, Bruker AXS Inc., Madison, 2001.
184. M. C. Burla, M. Camalli, B. Carrozzini, G. L. Cascarano, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Cryst. 2003, 36, 1103.
185. G. M. Sheldrick, SHELXL97, University of Göttingen, Göttingen, 1997.