Stability and reactivity of N-heterocyclic carbene complexes

Coordination Chemistry Reviews

Volumn 248, Issue 21-24, 2004, Pages 2247-2273

  Crudden, Cathleen M ^a   Allen, Daryl P ^a  

^a QUEEN S UNIVERSITY   (Canada)

Author keywords

Catalysis; Late transition metal complexes; N heterocyclic carbenes; Suzuki coupling reactions

Indexed keywords

ALKYL GROUP; CARBENOID; COBALT; HETEROCYCLIC COMPOUND; IMIDAZOLE DERIVATIVE; LIGAND; METAL COMPLEX; NICKEL; PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM; RUTHENIUM; TRANSITION ELEMENT;

ADDITION REACTION; CATALYSIS; CHELATION; CHEMICAL REACTION; COMPLEX FORMATION; DECOMPOSITION; METASTASIS; OXIDATION; PHASE TRANSITION; REDUCTION; REVIEW;

EID: 9744248685     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2004.05.013     Document Type: Review

References (196)

1. A.A. Danopoulos, N. Tsoureas, J.C. Green, M.B. Hursthouse, Chem. Commun. (2003) 756.
2. Öfele K. J. Organomet. Chem. 12:1968;42
3. Wanzlick H.W., Schönherr H.J. Angew. Chem. Int. Ed. Engl. 7:1968;141
4. Cardin D.J., Cetinkaya B., Lappert M.F. Chem. Rev. 72:1972;545
5. M.J. Doyle, M.F. Lappert, J. Chem. Soc., Chem. Commun. (1974) 679
6. M.J. Doyle, M.F. Lappert, G.M. McLaughlin, J. McMeeking, J. Chem. Soc., Dalton Trans. (1974) 1494
7. P.B. Hitchchock, M.F. Lappert, P.L. Pye, J. Chem. Soc., Dalton Trans. (1977) 2160
8. M.J. Doyle, M.F. Lappert, P.L. Pye, P. Terreros, J. Chem. Soc., Dalton Trans. (1984) 2355
9. Coleman A.W., Hitchcock P.B., Lappert M.F., Maskell R.K., Muller J.H. J. Organomet. Chem. 296:1985;173
10. Lappert M.F. J. Organomet. Chem. 358:1988;185
11. Cetinkaya B., Hitchcock P.B., Lappert M.F., Shaw D.B., Spyropoulos K., Warhurst N.J.W. J. Organomet. Chem. 459:1993;311
12. Cetinkaya E., Hitchcock P.B., Kucukbay H., Lappert M.F., Al-Juaid S. J. Organomet. Chem. 481:1994;89
13. Arduengo A.J. III, Harlow R.L., Kline M. J. Am. Chem. Soc. 113:1991;361
14. J.P. Collman, L.S. Hegedus, J.R. Norton, R.G. Finke (Eds.), Principles and Applications of Organotransition Metal Chemistry, University Science Books, California, 1987 (Chapter 16).
15. Scholl M., Trnka T.M., Morgan J.P., Grubbs R.H. Tetrahedron Lett. 40:1999;2247
16. Scholl M., Ding S., Lee C.W., Grubbs R.H. Org. Lett. 1:1999;953
17. Sanford M.S., Love J.A., Grubbs R.H. J. Am. Chem. Soc. 123:2001;6543
18. Trnka T.M., Morgan J.P., Sanford M.S., Wilhelm T.E., Scholl M., Choi T., Ding S., Day M.W., Grubbs R.H. J. Am. Chem. Soc. 125:2003;2546
19. Love J.A., Sanford M.S., Day M.W., Grubbs R.H. J. Am. Chem. Soc. 125:2003;10103
20. Seiders T.J., Williams D.W., Grubbs R.H. Org. Lett. 3:2001;3225
21. Weskamp T., Schattenmann W.C., Spiegler M., Herrmann W.A. Angew. Chem. Int. Ed. 37:1998;2490
22. Herrmann W.A. Angew. Chem. Int. Ed. 41:2002;1290. and references therein
23. Weskamp T., Kohl F.J., Hieringer W., Gleich D., Herrmann W.A. Angew. Chem. Int. Ed. 38:1999;2416
24. Ackermann L., Furstner A., Weskamp T., Kohl F.J., Herrmann W.A. Tetrahedron Lett. 40:1999;4787
25. Herrmann W.A., Elison M., Fischer J., Kocher C., Artus G.R.J. Angew. Chem. Int. Ed. Engl. 34:1995;2371
26. Herrmann W.A., Öfele K., Preysing D.v., Schneider S.K. J. Organomet. Chem. 687:2003;229. and references cited therein
27. Herrmann W.A., Reisinger C.-P., Spiegler M. J. Organomet. Chem. 557:1998;93
28. Gstöttmayr C.W.K., Böhm V.P.W., Herdtweck E., Grosche M., Herrmann W.A. Angew. Chem. Int. Ed. 41:2002;1363
29. Huang J., Stevens E.D., Nolan S.P., Petersen J.L. J. Am. Chem. Soc. 121:1999;2674
30. Viciu M.S., Germaneau R.F., Nolan S.P. Org. Lett. 4:2002;4053
31. Viciu M.S., Germaneau R.F., Navarro-Fernandez O., Stevens E.D., Nolan S.P. Organometallics. 21:2002;5470
32. Huang J., Schanz H.J., Stevens E.D., Nolan S.P. Organometallics. 18:1999;2370
33. Hillier A.C., Sommer W.J., Yong B.S., Petersen J.L., Cavallo L., Nolan S.P. Organometallics. 19:2003;4327
34. Navarro O., Kaur H., Mahjoor P., Nolan S.P. J. Org. Chem. 69:2004;3173
35. Fürstner A., Ackermann L., Gabor B., Goddard R., Lehmann C.W., Mynott R., Stelzer F., Thiel O.R. Chem. Eur. J. 7:2001;3236
36. Pruehs S., Lehmann C.W., Fürstner A. Organometallics. 23:2004;280
37. Fürstner A., Thiel O.R., Lehmann C.W. Organometallics. 21:2002;331
38. Fürstner A., Thiel O.R., Ackermann L., Schanz H.J., Nolan S.P. J. Org. Chem. 65:2000;2204
39. Ackermann L., Fürstner A., Weskamp T., Kohl F.J. Tetrahedron Lett. 40:1999;4787
40. Fürstner A., Thiel O.R., Ackermann L. Org. Lett. 3:2001;449
41. Fürstner A., Thiel O.R., Blanda G. Org. Lett. 2:2000;3731
42. Fürstner A., Radkowski K., Wirtz C., Goddard R., Lehmann C.W., Mynott R. J. Am. Chem. Soc. 124:2002;7061
43. Aïssa C., Riveiros R., Ragot J., Fürstner A. J. Am. Chem. Soc. 125:2003;15512
44. Van Veldhuizen J.J., Gillingham D.G., Garber S.B., Kataoka O., Hoveyda A.H. J. Am. Chem. Soc. 125:2003;12502
45. Van Veldhuizen J.J., Garber S.B., Kingsbury J.S., Hoveyda A.H. J. Am. Chem. Soc. 124:2002;4954
46. Kingsbury J.S., Harrity J.P.A., Bonitatebus P.J., Hoveyda A.H. J. Am. Chem. Soc. 121:1999;791
47. Hoveyda A.H., Gillingham D.G., Van Veldhuizen J.J., Kataoka O., Garber S.B., Kingsbury J.S., Harrity J.P.A. Org. Biol. Chem. 2:2004;8
48. Garber S.B., Kingsbury J.S., Gray B.L., Hoveyda A.H. J. Am. Chem. Soc. 122:2000;8168
49. E. Peris, J.A. Loch, J. Mata, R.H. Crabtree, Chem. Commun. (2001) 201
50. A.C. Chen, C.M. Crudden, D.P. Allen, manuscript in preparation.
51. For applications to the Suzuki-Miyaura reaction see: G. Altenhoff, R. Goddard, C.W. Lehmann, F. Glorius, Angew. Chem. Int. Ed. 42 (2003) 3690
52. Zhang C., Huang J., Trudell M.L., Nolan S.P. J. Org. Chem. 64:1999;3804
53. Fürstner A., Leitner A. Synlett. 2:2001;290. See also Refs. [8g,h]
54. For the Sonogashira coupling see: M. Eckhardt, G.C. Fu, J. Am. Chem. Soc. 125 (2003) 13642
55. For the Kumada coupling see: A.C. Frisch, F. Rataboul, A. Zapf, M. Beller, J. Organomet. Chem. 687 (2003) 403
56. For aminations of aromatic halides see Ref. [18d] and S.R. Stauffer, S. Lee, J.P. Stambuli, S.I. Hauck, J.F. Hartwig, Org. Lett. 2 (2000) 1423
57. Viciu M.S., Kelly R.A. III, Stevens E.D., Naud F., Studer M., Nolan S.P. Org. Lett. 5:2003;1479
58. Cheng J., Trudell M.L. Org. Lett. 3:2001;1371
59. Huang J., Grasa G., Nolan S.P. Org. Lett. 1:1999;1307
60. Gradel B., Brenner E., Schneider R., Fort Y. Tetrahedron Lett. 42:2001;5689
61. Strieter E.R., Blackmond D.G., Buchwald S.L. J. Am. Chem. Soc. 125:2003;13978
62. Alcazar-Roman L.M., Hartwig J.F. J. Am. Chem. Soc. 123:2001;12905
63. Louie J., Paul F., Hartwig J.F. Organometallics. 15:1996;2794
64. Hartwig J.F. Angew. Chem. Int. Ed. 37:1998;2047. See also Refs. [23-25]
65. Diggle R.A., Macgregor S.A., Whittlesey M.K. Organometallics. 23:2004;1857
66. Herrmann W.A., Köcher C. Angew. Chem. Int. Ed. 36:1997;2163
67. Westcamp T., Böhm V.P.W., Herrmann W.A. J. Organomet. Chem. 600:2000;12
68. Bourissou D., Guerret O., Gabbai F.P., Bertrand G. Chem. Rev. 100:2000;39
69. Gardiner M.G., Herrmann W.A., Reisinger C.P., Schwarz J., Spiegler M. J. Organomet. Chem. 572:1999;239
70. Gardiner M.G., Herrmann W.A., Reisinger C.-P., Spiegler M. J. Organomet. Chem. 572:1999;239
71. Powell M.T., Hou D.R., Perry M.C., Cui X., Burgess K. J. Am. Chem. Soc. 123:2001;8878
72. Lee H.M., Jiang T., Stevens E.D., Nolan S.P. Organometallics. 20:2001;1255
73. Albrecht M., Miecznikowski J.R., Samuel A., Faller J.M., Crabtree R.H. Organometallics. 21:2002;3596
74. L.D. Vázquesz-Serrano, B.T. Owens, J.M. Buriak, Chem. Commun. (2002) 2518
75. Miecznikowski J.R., Crabtree R.H. Organometallics. 23:2004;629
76. Kuhl S., Schneider R., Fort Y. Organometallics. 22:2003;4184
77. V.K. Dioumaev, D.J. Szalda, J. Hanson, J.A. Franz, R.M. Bullock, Chem. Commun. (2003) 1670
78. Mas-Marza E., Poyatos M., Sanau M., Peris E. Inorg. Chem. 43:2004;2213
79. Kaur H., Zinn F.K., Stevens E.D., Nolan S.P. Organometallics. 23:2004;1157
80. K.H. Park, S.Y. Kim, S.U. Son, Y.K. Chung, Eur. J. Org. Chem. (2003) 4341
81. W.-L. Duan, M. Shi, G.-B. Rong, Chem. Commun. (2003) 2916
82. Sprengers J.W., Mars M.J., Duin M.A., Cavell K.J., Elsevier C.J. J. Organomet. Chem. 679:2003;149
83. Marko I.E., Sebastien S., Buisine O., Mignani G., Branlard P., Tinant B., Declercq J.-P. Science. 298:2002;204
84. Mas-Marzá E., Poyatos M., Sanaú M., Peris E. Organometallics. 23:2004;1857
85. Grasa G.A., Moore A., Martin K.L., Stevens E.D., Nolan S.P., Paquet V., Lebel H. J. Organomet. Chem. 658:2002;126
86. Van Rensburg H., Tooze R.P., Foster D.F., Slawin A.M.Z. Inorg. Chem. 43:2004;2468
87. Chen A.C., Ren L., Decken A., Crudden C.M. Organometallics. 19:2000;3459
88. Sato Y., Yoshino T., Mori M. Org. Lett. 5:2003;31
89. Metathesis catalysts have been immobilized via the alkylidene ligand: S. Varray, R. Lazaro, J. Martinez, F. Lamaty, Organometallics 22 (2003) 2426
90. J. Dowden, J. Savovíc Chem. Commun. (2001) 37
91. Barrett A.G.M., Cramp S.M., Roberts R.S. Org Lett. 1:1999;1083
92. Yao Q. Agnew. Chem. Int. Ed. 39:2000;3896
93. Connon S.J., Dunne A.M., Blechert S. Angew. Chem. Int. Ed. 41:2002;3835
94. Jafarpour L., Heck M.-P., Baylon C., Lee H.M., Mioskowski C., Nolan S.P. Organometallics. 21:2002;671
95. Kingsbury J.S., Garber S.B., Giftos J.M., Gray B.L., Okamoto M.M., Farrer R.A., Fourkas J.T., Hoveyda A.H. Angew. Chem. Int. Ed. 40:2001;4251
96. Immobilization via the NHC is much less common: B. Çetinkaya, N. Gürbüz, T. Seçkin, I. Özdemir, J. Mol. Catal. A: Chem. 184 (2002) 31
97. Schürer S.C., Gessler S., Buschmann N., Blechert S. Agnew. Chem. Int. Ed. 39:2000;3898
98. Schwarz J., Böhm V.P.W., Gardiner M.G., Grosche M., Herrmann W.A., Hieringer W., Raudaschl-Sieber G. Chem. Eur. J. 6:2000;1773
99. Mayr M., Buchmeiser M.R., Wurst K. Adv. Synth. Catal. 344:2002;712
100. Herrmann W.A., Goossen L.J., Artus G.R.J., Kocher C. Organometallics. 16:1997;2472
101. D. Enders, H. Gielen, J. Runsink, K. Breuer, S. Brode, K. Boehn, Eur. J. Inorg. Chem. (1998) 913
102. Clyne D.S., Jin J., Genest E., Gallucci J.C., RajanBabu T.V. Org. Lett. 2:2000;1125
103. Lee S., Hartwig J.F. J. Org. Chem. 66:2001;3402
104. Perry M.C., Cui X., Burgess K. Tetrahedron Asymm. 13:2002;1969
105. Perry M.C., Cui X., Powell M.T., Hou D.-R., Reibenspies J.H., Burgess K. J. Am. Chem. Soc. 125:2003;113
106. F. Glorius, G. Altenhoff, R. Goddard, C. Lehmann, Chem. Commum. (2002) 2704
107. Bonnet L.G., Douthwaite R.E., Hodgson R. Organometallics. 22:2003;4384
108. Bonnet L.G., Douthwaite R.E., Kariuki B.M. Organometallics. 22:2003;4187
109. Sato Y., Imakuni N., Mori M. Adv. Synth. Catal. 345:2003;488
110. Jensen D.R., Sigman M.S. Org. Lett. 5:2003;63
111. Seo H., Park H.-J., Kim B.Y., Lee J.H., Son S.U., Chung Y.K. Organometallics. 22:2003;618
112. Perry M.C., Burgess K. Tet. Asy. 14:2003;951. and references cited therein
113. Gischig S., Togni A. Organometallics. 23:2004;2479
114. Pd-C(NHC) bond lengths are 1.95-2.07 Å compared to Pd-C(alkyl) and Pd-C(aryl) of 1.99-2.05 Å, data from Ref. [8e], and references therein
115. See also C. Boehme, G. Frenking, Organometallics 17 (1998) 5801, for a detailed discussion of bonding.
116. McGuinness D.S., Green M.J., Cavell K.J., Skelton B.W., White A.H. J. Organomet. Chem. 565:1998;165
117. McGuinness D.S., Saendig N., Yates B.F., Cavell K.J. J. Am. Chem. Soc. 123:2001;4029
118. Tatsumi K., Hoffmann R., Yamamoto A., Stille J.K. Bull. Chem. Soc. Jpn. 54:1981;1857
119. Loar M.K., Stille J.K. J. Am. Chem. Soc. 103:1981;4174
120. McGuinness D.S., Cavell K.J., Skelton B.W., White A.H. Organometallics. 18:1999;1596
121. Caddick S., Cloke F.G.N., Hitchcock P.B., Leonard J., de A.K., Lewis K., McKerrecher D., Titcomb L.R. Organometallics. 21:2002;4318
122. de A.K., Lewis K., Caddick S., Cloke F.G.N., Billingham N.C., Hitchcock P.B., Leonard J. J. Am. Chem. Soc. 125:2003;10066. Note that all of the compounds isolated from oxidative addition in Cavell's studies also have a trans arrangement of aryl and halide ligands
123. Grasa G.A., Viciu M.S., Huang J., Nolan S.P. J. Org. Chem. 66:2001;7729
124. Marshall W.J., Grushin V.V. Organometallics. 22:2003;1591
125. McGuinness D.S., Cavell K.J. Organometallics. 19:2000;4918
126. R.E. Douthwaite, M.L.H. Green, P.J. Silcock, P.T. Gomesc, J. Chem. Soc., Dalton Trans. (2002) 1386.
127. A.A.D. Tulloch, A.A. Danopoulos, R.P. Tooze, S.M. Cafferkey, S. Kleinhenza, M.B. Hursthouse, Chem. Commun. (2000) 1247.
128. Douthwaite R.E., Green M.L.H., Silcock P.J., Gomes P.T. Organometallics. 20:2001;2611
129. - counterion which promotes the exchange.
130. Nielsen D.J., Cavell K.J., Skelton B.W., White A.H. Inorg. Chim. Acta. 327:2002;116
131. D.J. Nielsen, A.M. Magill, B.F. Yates, K.J. Cavell, B.W. Skelton, A.H. White, Chem. Commun. (2002) 2500.
132. Magill A.M., McGuinness D.S., Cavell K.J., Britovsek G.J.P., Gibson V.C., White A.J.P., Williams D.J., White A.H., Skelton B.W. J. Organomet. Chem. 617-618:2001;546
133. McGuinness D.S., Cavell K.J. Organometallics. 19:2000;741
134. Martin H.C., James N.H., Aitken J., Gaunt J.A., Adams H., Haynes A. Organometallics. 22:2003;4451
135. Gonsalvi L., Gaunt J.A., Adams H., Castro A., Sunley G.J., Haynes A. Organometallics. 22:2003;1047
136. R.H. Crabtree (Ed.), The Organometallic Chemistry of the Transition Metals, third ed., John Wiley & Sons, New York, 2001, p. 166.
137. S. Bhaduri, D. Mukesh (Eds.), Homogeneous Catalysis: Mechanisms and Industrial Applications, Wiley-Interscience, Toronto, 2000 (Chapter 4).
138. Nielsen D.J., Cavell K.J., Skelton B.W., White A.H. Inorg. Chim. Acta. 352:2003;143
139. Denk M.K., Rodezno J.M. J. Organomet. Chem. 617-618:2001;737
140. L.R. Titcomb, S. Caddick, F.G.N. Cloke, D.J. Wilsona, D. McKerrecher, Chem. Commun. (2001) 1388.
141. Simms R.W., Drewitt M.J., Baird M.C. Organometallics. 21:2002;2958
142. Bryndza H.E., Evitt E.R., Bergman R.G. J. Am. Chem. 102:1980;4948
143. Weskamp T., Kohl F.J., Herrmann W.A. J. Organomet. Chem. 582:1999;362
144. Huang J., Stevens E.D., Nolan S.P., Petersen J.L. J. Am. Chem. Soc. 121:1999;2674
145. Bielawski C.W., Grubbs R.H. Angew. Chem. Int. Ed. 39:2000;2903
146. Drouin S.D., Zamanian F., Fogg D.E. Organometallics. 20:2001;5495
147. Drouin S.D., Yap G.P.A., Fogg D.E. Inorg. Chem. 39:2000;5412
148. P.B. Hitchcock, M.F. Lappert, P.L Pye, J. Chem. Soc., Dalton Trans. (1978) 826.
149. D. Allen, C.M. Crudden, L.A. Calhoun, R. Wang, J. Organomet. Chem. 2004, in press.
150. Jazzar R.F.R., Macgregor S.A., Mahon M.F., Richards S.P., Whittlesey M.K. J. Am. Chem. Soc. 124:2002;4944
151. Chilvers M.J., Jazzar R.F.R., Mahon M.F., Whittlesey M.K. Adv. Synth. Catal. 345:2003;1111
152. B. Chaudret, G. Commenges, R. Poilblanc, J. Chem. Soc., Chem. Commun. (1983) 641.
153. Chaudret B., Poilblanc R. Organometallics. 4:1985;1722
154. Giunta D., Hölscher M., Lehmann C.W., Mynott R., Wirtz C., Leitner W. Adv. Synth. Catal. 345:2003;1139
155. Prinz M., Grosche M., Herdtweck E., Herrmann W.A. Organometallics. 19:2000;1692
156. A.A. Danopoulos, S. Winston, M.B. Hursthouse, J. Chem. Soc., Dalton Trans. (2000) 3090.
157. Hitchcock P.B., Lappert M.F., Terreros P. J. Organomet. Chem. 239:1982;C26
158. Huang J., Stevens E.D., Nolan S.P. Organometallics. 19:2000;1194
159. Dorta R., Stevens E.D., Nolan S.P. J. Am. Chem. Soc. 126:2004;5054
160. Herrmann W.A., Goosen L.J., Spiegler M. Organometallics. 17:1998;2162
161. A.C. Chen, C.M. Crudden, unpublished results.
162. Boehme C., Frenking G. Organometallics. 15:1996;2039. and references therein
163. Arduengo A.J. III, Rasika Dias H.V., Dixon D.A., Harlow R.L., Klooster W.T., Koetzle T.F. J. Am. Chem. Soc. 116:1994;6812
164. Arduengo A.J. III, Davidson F., Dias H.V.R., Goerlich J.R., Krafczyk R., Marshall W.J., Prakasha T.K. J. Am. Chem. Soc. 119:1997;12742
165. Arduengo A.J. III, Calabrese J.C., Davidson F., Rasika Dias H.V., Goerlich J.R., Khasnis D., Marshall W.J., Tam M., Schmutzler R. Helv. Chim. Acta. 82:1999;2348
166. Cole M.L., Jones C., Junk P.C. New J. Chem. 262:2002;1296. and references therein
167. S. Gründemann, A. Kovacevic, M. Albrecht, J.W. Faller, R.H. Crabtree, Chem. Commun. (2001) 2274
168. Gründemann S., Kovacevic A., Albrecht M., Faller J.W., Crabtree R.H. J. Am. Chem. Soc. 124:2002;10473
169. Herrmann W.A., Roesky P.W., Elison M., Artus G.R.J., Öfele K. Organometallics. 14:1995;1085
170. Lebel H., Janes M.K., Charette A.B., Nolan S.P. J. Am. Chem. Soc. 126:2004;5046
171. Carmichael A.J., Earle M.J., Holbrey J.D., McCormac P.B., Seddon K.R. Org. Lett. 1:1999;997
172. D.S. McGuinness, K.J. Cavell, B.F. Yates, Chem. Commun. (2001) 355.
173. McGuinness D.S., Cavell K.J., Yates B.F., Skelton B.W., White A.H. J. Am. Chem. Soc. 123:2001;8317
174. Fürstner A., Seidel G., Kremzow D., Lehmann C.W. Organometallics. 22:2003;907
175. Isobe T., Ishikawa T. J. Org. Chem. 64:1999;5832
176. Isobe T., Ishikawa T. J. Org. Chem. 64:1999;6984
177. M.A. Duin, N.D. Clement, K.J. Cavell, C.J. Elsevier, Chem. Commun. 400 (2003).
178. Ma Y., Song C., Jiang W., Xue G., Cannon J.F., Wang X., Andrus M.B. Org. Lett. 5:2003;4635
179. Tan K.L., Bergman R.G., Ellman J.A. J. Am. Chem. Soc. 124:2002;13964
180. Tan K.L., Vasudevan A., Bergman R.G., Ellman J.A., Souers A.J. Org. Lett. 5:2003;2131
181. Lewis J.C., Wiedemann S.H., Bergman R.G., Ellman J.A. Org. Lett. 6:2004;35
182. S. Gründemann, M. Albrecht, A. Kovacevic, J.W. Faller, R.H. Crabtree, J. Chem. Soc., Dalton Trans. (2002) 2163
183. A. Kovacevic, S. Gründemann, J.R. Miecznikowski, E. Clot, O. Eisenstein, R.H. Crabtree, Chem. Commun. (2002) 2580
184. Chianese A.R., Kovacevic A., Zeglis B.M., Faller J.W., Crabtree R.H. Organometallics. 23:2004;2461. The following publication describing C-H activation at C-5 appeared during the preparation of the proofs of this manuscript
185. Hu X., Castro-Rodriguez I., Meyer K. Organometallics. 22:2003;3016
186. Danopoulos A.A., Tsoureas N., Wright J.A., Light M.E. Organometallics. 23:2004;166
187. Wassercheid P., Keim W. Angew. Chem. Int. Ed. 39:2000;3772
188. Welton T. Chem. Rev. 99:1999;2071
189. Xu L., Chen W., Xiao J. Organometallics. 19:2000;1123
190. Mathews C.J., Smith P.J., Welton T., White A.J.P., Williams D.J. Organometallics. 20:2001;3848
191. S. Bhaduri, D. Mukesh (Eds.), Homogeneous Catalysis: Mechanisms and Industrial Applications, Wiley-Interscience, Toronto, 2000, p. 139.
192. McGuinness D.S., Mueller W., Wasserscheid P., Cavell K.J., Skelton B.W., White A.H., Englert U. Organometallics. 21:2002;175
193. Audic N., Clavier H., Mauduit M., Guillemin J.C. J. Am. Chem. Soc. 125:2003;9248
194. Denk M.K., Rodezno J.M., Gupta S., Lough A.J. J. Organomet. Chem. 617-618:2001;242
195. Dible B.R., Sigman M.S. J. Am. Chem. Soc. 125:2003;872
196. Muehlhofer M., Strassner T., Herrmann W.A. Angew. Chem. Int. Ed. 41:2002;1745