Catalytic σ-bond metathesis

Structure and Bonding

Volumn 137, Issue , 2010, Pages 1-48

  Reznichenko, Alexander L ^a   Hultzsch, Kai C ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

C H activation; Catalysis; Cyclization; Hydroalkoxylation; Hydroamination; Hydroboration; Hydrogenation; Hydrophosphination; Hydrosilylation; Hydrostannation

Indexed keywords

EID: 78649901121     PISSN: 00815993     EISSN: 16168550     Source Type: Book Series    
DOI: 10.1007/430_2010_17     Document Type: Article

References (221)

1. Wailes PC, Weigold H, Bell AP (1972) J Organomet Chem 43:C32
2. Erker G (1977) J Organomet Chem 134:189
3. Arndtsen BA, Bergman RG, Mobley TA, Peterson TH (1995) Acc Chem Res 28:154
4. Vitale AA, San Filippo J (1982) J Am Chem Soc 104:7341
5. Gell KI, Posin B, Schwartz J, Williams GM (1982) J Am Chem Soc 104:1846
6. Watson PL, Parshall GW (1985) Acc Chem Res 18:51
7. Ziegler T, Folga E, Berces A (1993) J Am Chem Soc 115:636
8. Eisenstein O, Maron L (2002) J Organomet Chem 647:190
9. Sadow AD, Tilley TD (2005) J Am Chem Soc 127:643
10. Barros N, Eisenstein O, Maron L (2006) Dalton Trans:3052
11. Jones WD (2000) Science 287:1942
12. Labinger JA, Bercaw JE (2002) Nature 417:507
13. Lin Z (2007) Coord Chem Rev 251:2280
14. Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749
15. Maron L, Perrin L, Eisenstein O (2002) Dalton Trans:534
16. Perrin L, Maron L, Eisenstein O (2002) Inorg Chem 41:4355
17. Hunt PA (2007) Dalton Trans:1743
18. Zhou X, Zhu M (2002) J Organomet Chem 647:28
19. Molander GA, Dowdy ED (1999) Top Organomet Chem 2:119
20. Molander GA, Romero JAC (2002) Chem Rev 102:2161
21. Yasuda H (1999) Top Organomet Chem 2:255
22. Hou Z, Wakatsuki Y (2002) Coord Chem Rev 231:1
23. Gromada J, Carpentier J-F, Mortreux A (2004) Coord Chem Rev 248:397
24. Hou Z, Luo Y, Li X (2006) J Organomet Chem 691:3114
25. Jeske G, Lauke H, Mauermann H, Schumann H, Marks TJ (1985) J Am Chem Soc 107:8111
26. Molander GA, Hoberg JO (1992) J Org Chem 57:3266
27. Giardello MA, Conticello VP, Brard L, Gagńe MR, Marks TJ (1994) J Am Chem Soc 116:10241
28. Giardello MA, Conticello VP, Brard L, Sabat M, Rheingold AL, Stern CL, Marks TJ (1994) J Am Chem Soc 116:10212
29. Fu P-F, Brard L, Li Y, Marks TJ (1995) J Am Chem Soc 117:7157
30. Piers WE, Bercaw JE (1990) J Am Chem Soc 112:9406
31. Molander GA, Hoberg JO (1992) J Am Chem Soc 114:3123
32. Haar CM, Stern CL, Marks TJ (1996) Organometallics 15:1765
33. Jones GR, Landais Y (1996) Tetrahedron 52:7599
34. Voskoboynikov AZ, Parshina IN, Shestakova AK, Butin KP, Beletskaya IP, Kuz'mina LG, Howard JAK (1997) Organometallics 16:4041
35. Voskoboynikov AZ, Shestakova AK, Beletskaya IP (2001) Organometallics 20:2794
36. Forsyth CM, Nolan SP, Marks TJ (1991) Organometallics 10:2543
37. Radu NS, Tilley TD, Rheingold AL (1992) J Am Chem Soc 114:8293
38. Radu NS, Tilley TD (1995) J Am Chem Soc 117:5863
39. Tilley TD (1993) Acc Chem Res 26:22
40. Watson PL, Tebbe FN (1990) (du Pont de Nemours, E. I., and Co., USA). US Patent 4,965,386
41. Beletskaya IP, Voskoboinikov AZ, Parshina IN, Magomedov GK-I (1990) Russ Chem Bull 39:613
42. Sakakura T, Lautenschlager H-J, Tanaka M (1991) J Chem Soc Chem Commun:40
43. Onozawa S-Y, Sakakura T, Tanaka M (1994) Tetrahedron Lett 35:8177
44. Molander GA, Julius M (1992) J Org Chem 57:6347
45. Molander GA, Dowdy ED, Noll BC (1998) Organometallics 17:3754
46. Fu P-F (2006) J Mol Catal A Chem 243:253
47. Molander GA, Winterfeld J (1996) J Organomet Chem 524:275
48. Trifonov AA, Spaniol TP, Okuda J (2001) Organometallics 20:4869
49. Tardif O, Nishiura M, Hou Z (2003) Tetrahedron 59:10525
50. Trifonov AA, Spaniol TP, Okuda J (2004) Dalton Trans:2245
51. Robert D, Trifonov AA, Voth P, Okuda J (2006) J Organomet Chem 691:4393
52. Hou Z, Zhang Y, Tardif O, Wakatsuki Y (2001) J Am Chem Soc 123:9216
53. Gountchev TI, Tilley TD (1999) Organometallics 18:5661
54. Takaki K, Sonoda K, Kousaka T, Koshoji G, Shishido T, Takehira K (2001) Tetrahedron Lett 42:9211
55. Takaki K, Komeyama K, Takehira K (2003) Tetrahedron 59:10381
56. Gribkov DV, Hampel F, Hultzsch KC (2004) Eur J Inorg Chem:4091
57. Rasẗatter M, Zulys A, Roesky PW (2006) Chem Commun:874
58. Rasẗatter M, Zulys A, Roesky PW (2007) Chem Eur J 13:3606
59. Elvidge BR, Arndt S, Spaniol TP, Okuda J (2006) Dalton Trans:890
60. Konkol M, Kondracka M, Voth P, Spaniol TP, Okuda J (2008) Organometallics 27:3774
61. Ge S, Meetsma A, Hessen B (2008) Organometallics 27:3131
62. Horino Y, Livinghouse T (2004) Organometallics 23:12
63. Lyubov DM, Bubnov AM, Fukin GK, Dolgushin FM, AntipinMY, Pelce O, Schappacher M, Guillaume SM, Trifonov AA (2008) Eur J Inorg Chem:2090
64. Hultzsch KC, Voth P, Beckerle K, Spaniol TP, Okuda J (2000) Organometallics 19:228
65. Heeres HJ, Heeres A, Teuben JH (1990) Organometallics 9:1508
66. Heeres HJ, Teuben JH (1991) Organometallics 10:1980
67. Molander GA, Retsch WH (1995) Organometallics 14:4570
68. Molander GA, Retsch WH (1997) J Am Chem Soc 119:8817
69. Molander GA, Romero JAC, Corrette CP (2002) J Organomet Chem 647:225
70. Retsch WH (1997) PhD thesis, University of Colorado at Boulder
71. Molander GA, Nichols PJ (1995) J Am Chem Soc 117:4415
72. Molander GA, Romero JAC (2005) Tetrahedron 61:2631
73. Molander GA, Nichols PJ, Noll BC (1998) J Org Chem 63:2292
74. Molander GA, Dowdy ED (1998) J Org Chem 63:3386
75. Muci AR, Bercaw JE (2000) Tetrahedron Lett 41:7609
76. Smith ND, Mancuso J, Lautens M (2000) Chem Rev 100:3257
77. Voskoboynikov AZ, Beletskaya IP (1995) New J Chem 19:723
78. Burgess K, Ohlmeyer MJ (1991) Chem Rev 91:1179
79. Miyaura N (2001) In: Togni A, Gr̈utzmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 1
80. Harrison KN, Marks TJ (1992) J Am Chem Soc 114:9220
81. Bijpost EA, Duchateau R, Teuben JH (1995) J Mol Catal A Chem 95:121
82. Horino Y, Livinghouse T, Stan M (2004) Synlett:2639
83. Molander GA, Pfeiffer D (2001) Org Lett 3:361
84. Evans DA, Muci AR, Stuermer R (1993) J Org Chem 58:5307
85. M̈uller TE, Beller M (1998) Chem Rev 98:675
86. Brunet JJ, Neibecker D (2001) In:Togni A, Gr̈utzmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 91
87. Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079
88. M̈uller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795
89. Doye S (2009) In: Enders, D (ed) Science of synthesis, vol 40a. Thieme, Stuttgart, p 241
90. Roesky PW, M̈uller TE (2003) Angew Chem Int Ed 42:2708
91. Hultzsch KC (2005) Adv Synth Catal 347:367
92. Hultzsch KC (2005) Org Biomol Chem 3:1819
93. Aillaud I, Collin J, Hannedouche J, Schulz E (2007) Dalton Trans:5105
94. Zi G (2009) Dalton Trans:9101
95. Chemler SR (2009) Org Biomol Chem 7:3009
96. Reznichenko AL, Hultzsch KC (2010) In: Nugent TC (ed) Chiral amine synthesis: methods, developments and applications. Wiley, Weinheim, p 341
97. Hong S, Marks TJ (2004) Acc Chem Res 37:673
98. Li Y, Marks TJ (1996) Organometallics 15:3770
99. Li Y, Marks TJ (1998) J Am Chem Soc 120:1757
100. Ryu J-S, Li GY, Marks TJ (2003) J Am Chem Soc 125:12584
101. Gribkov DV, Hultzsch KC, Hampel F (2006) J Am Chem Soc 128:3748
102. Yuen HF, Marks TJ (2009) Organometallics 28:2423
103. Gagńe MR, Stern CL, Marks TJ (1992) J Am Chem Soc 114:275
104. Ryu J-S, Marks TJ, McDonald FE (2004) J Org Chem 69:1038
105. Li Y, Fu P-F, Marks TJ (1994) Organometallics 13:439
106. Li Y, Marks TJ (1996) J Am Chem Soc 118:9295
107. Hong S, Marks TJ (2002) J Am Chem Soc 124:7886
108. Hong S, Kawaoka AM, Marks TJ (2003) J Am Chem Soc 125:15878
109. Motta A, Lanza G, Fragal̀a IL, Marks TJ (2004) Organometallics 23:4097
110. Motta A, Fragal̀a IL, Marks TJ (2006) Organometallics 25:5533
111. Tobisch S (2005) J Am Chem Soc 127:11979
112. Tobisch S (2005) Chem Eur J 11:6372
113. Tobisch S (2006) Chem Eur J 12:2520
114. Gagńe MR, Marks TJ (1989) J Am Chem Soc 111:4108
115. Gribkov DV, Hultzsch KC, Hampel F (2003) Chem Eur J 9:4796
116. Hultzsch KC, Hampel F, Wagner T (2004) Organometallics 23:2601
117. Jung ME, Piizzi G (2005) Chem Rev 105:1735
118. Tian S, Arredondo VM, Stern CL, Marks TJ (1999) Organometallics 18:2568
119. Panda TK, Hrib CG, Jones PG, Jenter J, Roesky PW, TammM(2008) Eur J Inorg Chem:4270
120. Yuen HF, Marks TJ (2008) Organometallics 27:155
121. Xu X, Chen Y, Feng J, Zou G, Sun J (2010) Organometallics 29:549
122. B̈urgstein MR, Berberich H, Roesky PW (2001) Chem Eur J 7:3078
123. Kim YK, Livinghouse T, Bercaw JE (2001) Tetrahedron Lett 42:2933
124. Quinet C, Ates A, Marḱo IE (2008) Tetrahedron Lett 49:5032
125. Kim YK, Livinghouse T (2002) Angew Chem Int Ed 41:3645
126. Kim YK, Livinghouse T, Horino Y (2003) J Am Chem Soc 125:9560
127. Kim JY, Livinghouse T (2005) Org Lett 7:4391
128. B̈urgstein MR, Berberich H, Roesky PW (1998) Organometallics 17:1452
129. Zulys A, Panda TK, Gamer MT, Roesky PW (2004) Chem Commun:2584
130. Panda TK, Zulys A, Gamer MT, Roesky PW (2005) Organometallics 24:2197
131. Panda TK, Zulys A, Gamer MT, Roesky PW (2005) J Organomet Chem 690:5078
132. Lauterwasser F, Hayes PG, Br̈ase S, Piers WE, Schafer LL (2004) Organometallics 23:2234
133. Lu E, Gan W, Chen Y (2009) Organometallics 28:2318
134. Bambirra S, Tsurugi H, van Leusen D, Hessen B (2006) Dalton Trans:1157
135. Ge S, Meetsma A, Hessen B (2008) Organometallics 27:5339
136. Stanlake LJE, Schafer LL (2009) Organometallics 28:3990
137. Pawlikowski AV, Ellern A, Sadow AD (2009) Inorg Chem 48:8020
138. Ryu J-S, Marks TJ, McDonald FE (2001) Org Lett 3:3091
139. Molander GA, Dowdy ED (1998) J Org Chem 63:8983
140. Molander GA, Dowdy ED (1999) J Org Chem 64:6515
141. Kim H, Livinghouse T, Shim JH, Lee SG, Lee PH (2006) Adv Synth Catal 348:701
142. Molander GA, Hasegawa H (2004) Heterocycles 64:467
143. Arredondo VM, McDonald FE, Marks TJ (1998) J Am Chem Soc 120:4871
144. Arredondo VM, McDonald FE, Marks TJ (1999) Organometallics 18:1949
145. Arredondo VM, Tian S, McDonald FE, Marks TJ (1999) J Am Chem Soc 121:3633
146. Gagńe MR, Brard L, Conticello VP, Giardello MA, Stern CL, Marks TJ (1992) Organometallics 11:2003
147. Douglass MR, Ogasawara M, Hong S, Metz MV, Marks TJ (2002) Organometallics 21:283
148. Vitanova DV, Hampel F, Hultzsch KC (2007) J Organomet Chem 692:4690
149. Hong S, Tian S, Metz MV, Marks TJ (2003) J Am Chem Soc 125:14768
150. O'Shaughnessy PN, Knight PD, Morton C, Gillespie KM, Scott P (2003) Chem Commun: 1770
151. O'Shaughnessy PN, Scott P (2003) Tetrahedron Asymmetry 14:1979
152. O'Shaughnessy PN, Gillespie KM, Knight PD,Munslow I, Scott P (2004) Dalton Trans:2251
153. Collin J, Daran J-D, Schulz E, Trifonov A (2003) Chem Commun:3048
154. Collin J, Daran J-D, Jacquet O, Schulz E, Trifonov A (2005) Chem Eur J 11:3455
155. Riegert D, Collin J, Meddour A, Schulz E, Trifonov A (2006) J Org Chem 71:2514
156. Riegert D, Collin J, Daran J-D, Fillebeen T, Schulz E, Lyubov D, Fukin G, Trifonov A (2007) Eur J Inorg Chem:1159
157. Hannedouche J, Aillaud I, Collin J, Schulz E, Trifonov A (2008) Chem Commun:3552
158. Aillaud I, Collin J, Duhayon C, Guillot R, Lyubov D, Schulz E, Trifonov A (2008) Chem Eur J 14:2189
159. Aillaud I, Lyubov D, Collin J, Guillot R, Hannedouche J, Schulz E, Trifonov A (2008) Organometallics 27:5929
160. Aillaud I, Wright K, Collin J, Schulz E, Mazaleyrat J-P (2008) Tetrahedron Asymmetry 19:82
161. Kim JY, Livinghouse T (2005) Org Lett 7:1737
162. Kim H, Kim YK, Shim JH, Kim M, Han M, Livinghouse T, Lee PH (2006) Adv Synth Catal 348:2609
163. Gribkov DV, Hultzsch KC (2004) Chem Commun:730
164. Meyer N, Zulys A, Roesky PW (2006) Organometallics 25:4179
165. Yu X, Marks TJ (2007) Organometallics 26:365
166. Heck R, Schulz E, Collin J, Carpentier J-F (2007) J Mol Catal A Chem 268:163
167. Xiang L, Wang Q, Song H, Zi G (2007) Organometallics 26:5323
168. Zi G, Xiang L, Song H (2008) Organometallics 27:1242
169. Wang Q, Xiang L, Song H, Zi G (2008) Inorg Chem 47:4319
170. Wang Q, Xiang L, Song H, Zi G (2009) J Organomet Chem 694:691
171. Reznichenko AL, Hampel F, Hultzsch KC (2009) Chem Eur J 15:12819
172. Obora Y, Ohta T, Stern CL, Marks TJ (1997) J Am Chem Soc 119:3745
173. Takaki K, Kamata T, Miura Y, Shishido T, Takehira K (1999) J Org Chem 64:3891
174. Li Y, Marks TJ (1996) J Am Chem Soc 118:707
175. Molander GA, Pack SK (2003) J Org Chem 68:9214
176. Molander GA, Pack SK (2003) Tetrahedron 59:10581
177. Tanaka M (2004) Top Curr Chem 232:25
178. Douglass MR, Marks TJ (2000) J Am Chem Soc 122:1824
179. Douglass MR, Stern CL, Marks TJ (2001) J Am Chem Soc 123:10221
180. Kawaoka AM, Douglass MR, Marks TJ (2003) Organometallics 22:4630
181. Motta A, Fragal̀a IL, Marks TJ (2005) Organometallics 24:4995
182. Issleib K, K̈ummel R (1965) J Organomet Chem 3:84
183. Nolan SP, Stern, D, Hedden, D, Marks, TJ (1990) ACS Symp Ser 428:159
184. Baechler RD, Mislow K (1970) J Am Chem Soc 92:3090
185. Takaki K, Takeda M, Koshoji G, Shishido T, Takehira K (2001) Tetrahedron Lett 42:6357
186. Takaki K, Koshoji G, Komeyama K, Takeda M, Shishido T, Kitani A, Takehira K (2003) J Org Chem 68:6554
187. Takaki K, Komeyama K, Kobayashi D, Kawabata T, Takehira K (2006) J Alloys Compd: 408-412, 432
188. Komeyama K, Kobayashi D, Yamamoto Y, Takehira K, Takaki K (2006) Tetrahedron 62:2511
189. Mercy M, Maron L (2009) Dalton Trans:3014
190. Tani K, Kataoka Y (2001) In: Togni A, Gr̈utzmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 171
191. Yu X, Seo S, Marks TJ (2007) J Am Chem Soc 129:7244
192. Seo S, Yu X, Marks TJ (2009) J Am Chem Soc 131:263
193. Dzudza A, Marks TJ (2009) Org Lett 11:1523
194. Haber S, RegitzM(1997) In: de Meijere A (ed) Houben-Weyl methods of organic chemistry, vol 17f. Thieme, New York, p 1051
195. Thompson ME, Baxter SM, Bulls AR, Burger BJ, Nolan MC, Santarsiero BD, Schaefer WP, Bercaw JE (1987) J Am Chem Soc 109:203
196. St. Clair M, Schaefer WP, Bercaw JE (1991) Organometallics 10:525
197. Den Haan KH, Wielstra Y, Teuben JH (1987) Organometallics 6:2053
198. Heeres HJ, Nijhoff J, Teuben JH, Rogers RD (1993) Organometallics 12:2609
199. Evans WJ, Keyer RA, Ziller JW (1993) Organometallics 12:2618
200. Schaverien CJ (1994) Organometallics 13:69
201. Duchateau R, van Wee CT, Teuben JH (1996) Organometallics 15:2291
202. Ge S, Meetsma A, Hessen B (2009) Organometallics 28:719
203. Nishiura M, Hou Z, Wakatsuki Y, Yamaki T, Miyamoto T (2003) J Am Chem Soc 125:1184
204. Kretschmer WP, Troyanov SI, Meetsma A, Hessen B, Teuben JH (1998) Organometallics 17:284
205. Tazelaar CGJ, Bambirra S, van Leusen D, Meetsma A, Hessen B, Teuben JH (2004) Organometallics 23:936
206. Komeyama K, Kawabata T, Takehira K, Takaki K (2005) J Org Chem 70:7260
207. Piers WE, Shapiro PJ, Bunel EE, Bercaw JE (1990) Synlett:74
208. Hajela S, Bercaw JE (1994) Organometallics 13:1147
209. Bercaw JE (1990) Pure Appl Chem 62:1151
210. Crabtree RH (2004) J Organomet Chem 689:4083
211. Sakaki S (2005) Top Organomet Chem 12:31
212. Watson PL (1983) J Am Chem Soc 105:6491
213. Watson PL (1983) J Chem Soc Chem Commun:276
214. Fendrick CM, Marks TJ (1986) J Am Chem Soc 108:425
215. Sherer EC, Cramer CJ (2003) Organometallics 22:1682
216. Woodrum NL, Cramer CJ (2006) Organometallics 25:68
217. Lewin JL, Woodrum NL, Cramer CJ (2006) Organometallics 25:5906
218. Sadow AD, Tilley TD (2003) Angew Chem Int Ed 42:803
219. Sadow AD, Tilley TD (2003) J Am Chem Soc 125:7971
220. Barros N, Eisenstein O, Maron L, Tilley TD (2006) Organometallics 25:5699
221. Barros N, Eisenstein O, Maron L, Tilley TD (2008) Organometallics 27:2252