Molecular Catalysis of Rare-Earth Elements pp 1-48

Part of the Structure and Bonding book series (STRUCTURE, volume 137) | Cite as

Catalytic σ-Bond Metathesis

Chapter

Abstract

This account summarizes information on recently reported applications of organo-rare-earth metal complexes in various catalytic transformations of small molecules. The σ-bond metathesis at d0rare-earth metal centers plays a pivotal role in carbon–carbon and carbon–heteroatom bond forming processes. Relevant mechanistic details are discussed and the focus of the review lies in practical applications of organo-rare-earth metal complexes.

Keywords

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

References

  1. 1.
    Wailes PC, Weigold H, Bell AP (1972) J Organomet Chem 43:C32Google Scholar
  2. 2.
    Erker G (1977) J Organomet Chem 134:189Google Scholar
  3. 3.
    Arndtsen BA, Bergman RG, Mobley TA, Peterson TH (1995) Acc Chem Res 28:154Google Scholar
  4. 4.
    Vitale AA, San Filippo J (1982) J Am Chem Soc 104:7341Google Scholar
  5. 5.
    Gell KI, Posin B, Schwartz J, Williams GM (1982) J Am Chem Soc 104:1846Google Scholar
  6. 6.
    Watson PL, Parshall GW (1985) Acc Chem Res 18:51Google Scholar
  7. 7.
    Ziegler T, Folga E, Berces A (1993) J Am Chem Soc 115:636Google Scholar
  8. 8.
    Eisenstein O, Maron L (2002) J Organomet Chem 647:190Google Scholar
  9. 9.
    Sadow AD, Tilley TD (2005) J Am Chem Soc 127:643Google Scholar
  10. 10.
    Barros N, Eisenstein O, Maron L (2006) Dalton Trans:3052Google Scholar
  11. 11.
    Jones WD (2000) Science 287:1942Google Scholar
  12. 12.
    Labinger JA, Bercaw JE (2002) Nature 417:507Google Scholar
  13. 13.
    Lin Z (2007) Coord Chem Rev 251:2280Google Scholar
  14. 14.
    Balcells D, Clot E, Eisenstein O (2010) Chem Rev 110:749Google Scholar
  15. 15.
    Maron L, Perrin L, Eisenstein O (2002) Dalton Trans:534Google Scholar
  16. 16.
    Perrin L, Maron L, Eisenstein O (2002) Inorg Chem 41:4355Google Scholar
  17. 17.
    Hunt PA (2007) Dalton Trans:1743Google Scholar
  18. 18.
    Zhou X, Zhu M (2002) J Organomet Chem 647:28Google Scholar
  19. 19.
    Molander GA, Dowdy ED (1999) Top Organomet Chem 2:119Google Scholar
  20. 20.
    Molander GA, Romero JAC (2002) Chem Rev 102:2161Google Scholar
  21. 21.
    Yasuda H (1999) Top Organomet Chem 2:255Google Scholar
  22. 22.
    Hou Z, Wakatsuki Y (2002) Coord Chem Rev 231:1Google Scholar
  23. 23.
    Gromada J, Carpentier J-F, Mortreux A (2004) Coord Chem Rev 248:397Google Scholar
  24. 24.
    Hou Z, Luo Y, Li X (2006) J Organomet Chem 691:3114Google Scholar
  25. 25.
    Jeske G, Lauke H, Mauermann H, Schumann H, Marks TJ (1985) J Am Chem Soc 107:8111Google Scholar
  26. 26.
    Molander GA, Hoberg JO (1992) J Org Chem 57:3266Google Scholar
  27. 27.
    Giardello MA, Conticello VP, Brard L, Gagné MR, Marks TJ (1994) J Am Chem Soc 116:10241Google Scholar
  28. 28.
    Giardello MA, Conticello VP, Brard L, Sabat M, Rheingold AL, Stern CL, Marks TJ (1994) J Am Chem Soc 116:10212Google Scholar
  29. 29.
    Fu P-F, Brard L, Li Y, Marks TJ (1995) J Am Chem Soc 117:7157Google Scholar
  30. 30.
    Piers WE, Bercaw JE (1990) J Am Chem Soc 112:9406Google Scholar
  31. 31.
    Molander GA, Hoberg JO (1992) J Am Chem Soc 114:3123Google Scholar
  32. 32.
    Haar CM, Stern CL, Marks TJ (1996) Organometallics 15:1765Google Scholar
  33. 33.
    Jones GR, Landais Y (1996) Tetrahedron 52:7599Google Scholar
  34. 34.
    Voskoboynikov AZ, Parshina IN, Shestakova AK, Butin KP, Beletskaya IP, Kuz’mina LG, Howard JAK (1997) Organometallics 16:4041Google Scholar
  35. 35.
    Voskoboynikov AZ, Shestakova AK, Beletskaya IP (2001) Organometallics 20:2794Google Scholar
  36. 36.
    Forsyth CM, Nolan SP, Marks TJ (1991) Organometallics 10:2543Google Scholar
  37. 37.
    Radu NS, Tilley TD, Rheingold AL (1992) J Am Chem Soc 114:8293Google Scholar
  38. 38.
    Radu NS, Tilley TD (1995) J Am Chem Soc 117:5863Google Scholar
  39. 39.
    Tilley TD (1993) Acc Chem Res 26:22Google Scholar
  40. 40.
    Watson PL, Tebbe FN (1990) (du Pont de Nemours, E. I., and Co., USA). US Patent 4,965,386Google Scholar
  41. 41.
    Beletskaya IP, Voskoboinikov AZ, Parshina IN, Magomedov GK-I (1990) Russ Chem Bull 39:613Google Scholar
  42. 42.
    Sakakura T, Lautenschlager H-J, Tanaka M (1991) J Chem Soc Chem Commun:40Google Scholar
  43. 43.
    Onozawa S-Y, Sakakura T, Tanaka M (1994) Tetrahedron Lett 35:8177Google Scholar
  44. 44.
    Molander GA, Julius M (1992) J Org Chem 57:6347Google Scholar
  45. 45.
    Molander GA, Dowdy ED, Noll BC (1998) Organometallics 17:3754Google Scholar
  46. 46.
    Fu P-F (2006) J Mol Catal A Chem 243:253Google Scholar
  47. 47.
    Molander GA, Winterfeld J (1996) J Organomet Chem 524:275Google Scholar
  48. 48.
    Trifonov AA, Spaniol TP, Okuda J (2001) Organometallics 20:4869Google Scholar
  49. 49.
    Tardif O, Nishiura M, Hou Z (2003) Tetrahedron 59:10525Google Scholar
  50. 50.
    Trifonov AA, Spaniol TP, Okuda J (2004) Dalton Trans:2245Google Scholar
  51. 51.
    Robert D, Trifonov AA, Voth P, Okuda J (2006) J Organomet Chem 691:4393Google Scholar
  52. 52.
    Hou Z, Zhang Y, Tardif O, Wakatsuki Y (2001) J Am Chem Soc 123:9216Google Scholar
  53. 53.
    Gountchev TI, Tilley TD (1999) Organometallics 18:5661Google Scholar
  54. 54.
    Takaki K, Sonoda K, Kousaka T, Koshoji G, Shishido T, Takehira K (2001) Tetrahedron Lett 42:9211Google Scholar
  55. 55.
    Takaki K, Komeyama K, Takehira K (2003) Tetrahedron 59:10381Google Scholar
  56. 56.
    Gribkov DV, Hampel F, Hultzsch KC (2004) Eur J Inorg Chem:4091Google Scholar
  57. 57.
    Rastätter M, Zulys A, Roesky PW (2006) Chem Commun:874Google Scholar
  58. 58.
    Rastätter M, Zulys A, Roesky PW (2007) Chem Eur J 13:3606Google Scholar
  59. 59.
    Elvidge BR, Arndt S, Spaniol TP, Okuda J (2006) Dalton Trans:890Google Scholar
  60. 60.
    Konkol M, Kondracka M, Voth P, Spaniol TP, Okuda J (2008) Organometallics 27:3774Google Scholar
  61. 61.
    Ge S, Meetsma A, Hessen B (2008) Organometallics 27:3131Google Scholar
  62. 62.
    Horino Y, Livinghouse T (2004) Organometallics 23:12Google Scholar
  63. 63.
    Lyubov DM, Bubnov AM, Fukin GK, Dolgushin FM, Antipin MY, Pelce O, Schappacher M, Guillaume SM, Trifonov AA (2008) Eur J Inorg Chem:2090Google Scholar
  64. 64.
    Hultzsch KC, Voth P, Beckerle K, Spaniol TP, Okuda J (2000) Organometallics 19:228Google Scholar
  65. 65.
    Heeres HJ, Heeres A, Teuben JH (1990) Organometallics 9:1508Google Scholar
  66. 66.
    Heeres HJ, Teuben JH (1991) Organometallics 10:1980Google Scholar
  67. 67.
    Molander GA, Retsch WH (1995) Organometallics 14:4570Google Scholar
  68. 68.
    Molander GA, Retsch WH (1997) J Am Chem Soc 119:8817Google Scholar
  69. 69.
    Molander GA, Romero JAC, Corrette CP (2002) J Organomet Chem 647:225Google Scholar
  70. 70.
    Retsch WH (1997) PhD thesis, University of Colorado at BoulderGoogle Scholar
  71. 71.
    Molander GA, Nichols PJ (1995) J Am Chem Soc 117:4415Google Scholar
  72. 72.
    Molander GA, Romero JAC (2005) Tetrahedron 61:2631Google Scholar
  73. 73.
    Molander GA, Nichols PJ, Noll BC (1998) J Org Chem 63:2292Google Scholar
  74. 74.
    Molander GA, Dowdy ED (1998) J Org Chem 63:3386Google Scholar
  75. 75.
    Muci AR, Bercaw JE (2000) Tetrahedron Lett 41:7609Google Scholar
  76. 76.
    Smith ND, Mancuso J, Lautens M (2000) Chem Rev 100:3257Google Scholar
  77. 77.
    Voskoboynikov AZ, Beletskaya IP (1995) New J Chem 19:723Google Scholar
  78. 78.
    Burgess K, Ohlmeyer MJ (1991) Chem Rev 91:1179Google Scholar
  79. 79.
    Miyaura N (2001) In: Togni A, Grützmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 1Google Scholar
  80. 80.
    Harrison KN, Marks TJ (1992) J Am Chem Soc 114:9220Google Scholar
  81. 81.
    Bijpost EA, Duchateau R, Teuben JH (1995) J Mol Catal A Chem 95:121Google Scholar
  82. 82.
    Horino Y, Livinghouse T, Stan M (2004) Synlett:2639Google Scholar
  83. 83.
    Molander GA, Pfeiffer D (2001) Org Lett 3:361Google Scholar
  84. 84.
    Evans DA, Muci AR, Stuermer R (1993) J Org Chem 58:5307Google Scholar
  85. 85.
    Müller TE, Beller M (1998) Chem Rev 98:675Google Scholar
  86. 86.
    Brunet JJ, Neibecker D (2001) In:Togni A, Grützmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 91Google Scholar
  87. 87.
    Alonso F, Beletskaya IP, Yus M (2004) Chem Rev 104:3079Google Scholar
  88. 88.
    Müller TE, Hultzsch KC, Yus M, Foubelo F, Tada M (2008) Chem Rev 108:3795Google Scholar
  89. 89.
    Doye S (2009) In: Enders, D (ed) Science of synthesis, vol 40a. Thieme, Stuttgart, p 241Google Scholar
  90. 90.
    Roesky PW, Müller TE (2003) Angew Chem Int Ed 42:2708Google Scholar
  91. 91.
    Hultzsch KC (2005) Adv Synth Catal 347:367Google Scholar
  92. 92.
    Hultzsch KC (2005) Org Biomol Chem 3:1819Google Scholar
  93. 93.
    Aillaud I, Collin J, Hannedouche J, Schulz E (2007) Dalton Trans:5105Google Scholar
  94. 94.
    Zi G (2009) Dalton Trans:9101Google Scholar
  95. 95.
    Chemler SR (2009) Org Biomol Chem 7:3009Google Scholar
  96. 96.
    Reznichenko AL, Hultzsch KC (2010) In: Nugent TC (ed) Chiral amine synthesis: methods, developments and applications. Wiley, Weinheim, p 341Google Scholar
  97. 97.
    Hong S, Marks TJ (2004) Acc Chem Res 37:673Google Scholar
  98. 98.
    Li Y, Marks TJ (1996) Organometallics 15:3770Google Scholar
  99. 99.
    Li Y, Marks TJ (1998) J Am Chem Soc 120:1757Google Scholar
  100. 100.
    Ryu J-S, Li GY, Marks TJ (2003) J Am Chem Soc 125:12584Google Scholar
  101. 101.
    Gribkov DV, Hultzsch KC, Hampel F (2006) J Am Chem Soc 128:3748Google Scholar
  102. 102.
    Yuen HF, Marks TJ (2009) Organometallics 28:2423Google Scholar
  103. 103.
    Gagné MR, Stern CL, Marks TJ (1992) J Am Chem Soc 114:275Google Scholar
  104. 104.
    Ryu J-S, Marks TJ, McDonald FE (2004) J Org Chem 69:1038Google Scholar
  105. 105.
    Li Y, Fu P-F, Marks TJ (1994) Organometallics 13:439Google Scholar
  106. 106.
    Li Y, Marks TJ (1996) J Am Chem Soc 118:9295Google Scholar
  107. 107.
    Hong S, Marks TJ (2002) J Am Chem Soc 124:7886Google Scholar
  108. 108.
    Hong S, Kawaoka AM, Marks TJ (2003) J Am Chem Soc 125:15878Google Scholar
  109. 109.
    Motta A, Lanza G, Fragalà IL, Marks TJ (2004) Organometallics 23:4097Google Scholar
  110. 110.
    Motta A, Fragalà IL, Marks TJ (2006) Organometallics 25:5533Google Scholar
  111. 111.
    Tobisch S (2005) J Am Chem Soc 127:11979Google Scholar
  112. 112.
    Tobisch S (2005) Chem Eur J 11:6372Google Scholar
  113. 113.
    Tobisch S (2006) Chem Eur J 12:2520Google Scholar
  114. 114.
    Gagné MR, Marks TJ (1989) J Am Chem Soc 111:4108Google Scholar
  115. 115.
    Gribkov DV, Hultzsch KC, Hampel F (2003) Chem Eur J 9:4796Google Scholar
  116. 116.
    Hultzsch KC, Hampel F, Wagner T (2004) Organometallics 23:2601Google Scholar
  117. 117.
    Jung ME, Piizzi G (2005) Chem Rev 105:1735Google Scholar
  118. 118.
    Tian S, Arredondo VM, Stern CL, Marks TJ (1999) Organometallics 18:2568Google Scholar
  119. 119.
    Panda TK, Hrib CG, Jones PG, Jenter J, Roesky PW, Tamm M (2008) Eur J Inorg Chem:4270Google Scholar
  120. 120.
    Yuen HF, Marks TJ (2008) Organometallics 27:155Google Scholar
  121. 121.
    Xu X, Chen Y, Feng J, Zou G, Sun J (2010) Organometallics 29:549Google Scholar
  122. 122.
    Bürgstein MR, Berberich H, Roesky PW (2001) Chem Eur J 7:3078Google Scholar
  123. 123.
    Kim YK, Livinghouse T, Bercaw JE (2001) Tetrahedron Lett 42:2933Google Scholar
  124. 124.
    Quinet C, Ates A, Markó IE (2008) Tetrahedron Lett 49:5032Google Scholar
  125. 125.
    Kim YK, Livinghouse T (2002) Angew Chem Int Ed 41:3645Google Scholar
  126. 126.
    Kim YK, Livinghouse T, Horino Y (2003) J Am Chem Soc 125:9560Google Scholar
  127. 127.
    Kim JY, Livinghouse T (2005) Org Lett 7:4391Google Scholar
  128. 128.
    Bürgstein MR, Berberich H, Roesky PW (1998) Organometallics 17:1452Google Scholar
  129. 129.
    Zulys A, Panda TK, Gamer MT, Roesky PW (2004) Chem Commun:2584Google Scholar
  130. 130.
    Panda TK, Zulys A, Gamer MT, Roesky PW (2005) Organometallics 24:2197Google Scholar
  131. 131.
    Panda TK, Zulys A, Gamer MT, Roesky PW (2005) J Organomet Chem 690:5078Google Scholar
  132. 132.
    Lauterwasser F, Hayes PG, Bräse S, Piers WE, Schafer LL (2004) Organometallics 23:2234Google Scholar
  133. 133.
    Lu E, Gan W, Chen Y (2009) Organometallics 28:2318Google Scholar
  134. 134.
    Bambirra S, Tsurugi H, van Leusen D, Hessen B (2006) Dalton Trans:1157Google Scholar
  135. 135.
    Ge S, Meetsma A, Hessen B (2008) Organometallics 27:5339Google Scholar
  136. 136.
    Stanlake LJE, Schafer LL (2009) Organometallics 28:3990Google Scholar
  137. 137.
    Pawlikowski AV, Ellern A, Sadow AD (2009) Inorg Chem 48:8020Google Scholar
  138. 138.
    Ryu J-S, Marks TJ, McDonald FE (2001) Org Lett 3:3091Google Scholar
  139. 139.
    Molander GA, Dowdy ED (1998) J Org Chem 63:8983Google Scholar
  140. 140.
    Molander GA, Dowdy ED (1999) J Org Chem 64:6515Google Scholar
  141. 141.
    Kim H, Livinghouse T, Shim JH, Lee SG, Lee PH (2006) Adv Synth Catal 348:701Google Scholar
  142. 142.
    Molander GA, Hasegawa H (2004) Heterocycles 64:467Google Scholar
  143. 143.
    Arredondo VM, McDonald FE, Marks TJ (1998) J Am Chem Soc 120:4871Google Scholar
  144. 144.
    Arredondo VM, McDonald FE, Marks TJ (1999) Organometallics 18:1949Google Scholar
  145. 145.
    Arredondo VM, Tian S, McDonald FE, Marks TJ (1999) J Am Chem Soc 121:3633Google Scholar
  146. 146.
    Gagné MR, Brard L, Conticello VP, Giardello MA, Stern CL, Marks TJ (1992) Organometallics 11:2003Google Scholar
  147. 147.
    Douglass MR, Ogasawara M, Hong S, Metz MV, Marks TJ (2002) Organometallics 21:283Google Scholar
  148. 148.
    Vitanova DV, Hampel F, Hultzsch KC (2007) J Organomet Chem 692:4690Google Scholar
  149. 149.
    Hong S, Tian S, Metz MV, Marks TJ (2003) J Am Chem Soc 125:14768Google Scholar
  150. 150.
    O’Shaughnessy PN, Knight PD, Morton C, Gillespie KM, Scott P (2003) Chem Commun:1770Google Scholar
  151. 151.
    O’Shaughnessy PN, Scott P (2003) Tetrahedron Asymmetry 14:1979Google Scholar
  152. 152.
    O’Shaughnessy PN, Gillespie KM, Knight PD, Munslow I, Scott P (2004) Dalton Trans:2251Google Scholar
  153. 153.
    Collin J, Daran J-D, Schulz E, Trifonov A (2003) Chem Commun:3048Google Scholar
  154. 154.
    Collin J, Daran J-D, Jacquet O, Schulz E, Trifonov A (2005) Chem Eur J 11:3455Google Scholar
  155. 155.
    Riegert D, Collin J, Meddour A, Schulz E, Trifonov A (2006) J Org Chem 71:2514Google Scholar
  156. 156.
    Riegert D, Collin J, Daran J-D, Fillebeen T, Schulz E, Lyubov D, Fukin G, Trifonov A (2007) Eur J Inorg Chem:1159Google Scholar
  157. 157.
    Hannedouche J, Aillaud I, Collin J, Schulz E, Trifonov A (2008) Chem Commun:3552Google Scholar
  158. 158.
    Aillaud I, Collin J, Duhayon C, Guillot R, Lyubov D, Schulz E, Trifonov A (2008) Chem Eur J 14:2189Google Scholar
  159. 159.
    Aillaud I, Lyubov D, Collin J, Guillot R, Hannedouche J, Schulz E, Trifonov A (2008) Organometallics 27:5929Google Scholar
  160. 160.
    Aillaud I, Wright K, Collin J, Schulz E, Mazaleyrat J-P (2008) Tetrahedron Asymmetry 19:82Google Scholar
  161. 161.
    Kim JY, Livinghouse T (2005) Org Lett 7:1737Google Scholar
  162. 162.
    Kim H, Kim YK, Shim JH, Kim M, Han M, Livinghouse T, Lee PH (2006) Adv Synth Catal 348:2609Google Scholar
  163. 163.
    Gribkov DV, Hultzsch KC (2004) Chem Commun:730Google Scholar
  164. 164.
    Meyer N, Zulys A, Roesky PW (2006) Organometallics 25:4179Google Scholar
  165. 165.
    Yu X, Marks TJ (2007) Organometallics 26:365Google Scholar
  166. 166.
    Heck R, Schulz E, Collin J, Carpentier J-F (2007) J Mol Catal A Chem 268:163Google Scholar
  167. 167.
    Xiang L, Wang Q, Song H, Zi G (2007) Organometallics 26:5323Google Scholar
  168. 168.
    Zi G, Xiang L, Song H (2008) Organometallics 27:1242Google Scholar
  169. 169.
    Wang Q, Xiang L, Song H, Zi G (2008) Inorg Chem 47:4319Google Scholar
  170. 170.
    Wang Q, Xiang L, Song H, Zi G (2009) J Organomet Chem 694:691Google Scholar
  171. 171.
    Reznichenko AL, Hampel F, Hultzsch KC (2009) Chem Eur J 15:12819Google Scholar
  172. 172.
    Obora Y, Ohta T, Stern CL, Marks TJ (1997) J Am Chem Soc 119:3745Google Scholar
  173. 173.
    Takaki K, Kamata T, Miura Y, Shishido T, Takehira K (1999) J Org Chem 64:3891Google Scholar
  174. 174.
    Li Y, Marks TJ (1996) J Am Chem Soc 118:707Google Scholar
  175. 175.
    Molander GA, Pack SK (2003) J Org Chem 68:9214Google Scholar
  176. 176.
    Molander GA, Pack SK (2003) Tetrahedron 59:10581Google Scholar
  177. 177.
    Tanaka M (2004) Top Curr Chem 232:25Google Scholar
  178. 178.
    Douglass MR, Marks TJ (2000) J Am Chem Soc 122:1824Google Scholar
  179. 179.
    Douglass MR, Stern CL, Marks TJ (2001) J Am Chem Soc 123:10221Google Scholar
  180. 180.
    Kawaoka AM, Douglass MR, Marks TJ (2003) Organometallics 22:4630Google Scholar
  181. 181.
    Motta A, Fragalà IL, Marks TJ (2005) Organometallics 24:4995Google Scholar
  182. 182.
    Issleib K, Kümmel R (1965) J Organomet Chem 3:84Google Scholar
  183. 183.
    Nolan SP, Stern, D, Hedden, D, Marks, TJ (1990) ACS Symp Ser 428:159Google Scholar
  184. 184.
    Baechler RD, Mislow K (1970) J Am Chem Soc 92:3090Google Scholar
  185. 185.
    Takaki K, Takeda M, Koshoji G, Shishido T, Takehira K (2001) Tetrahedron Lett 42:6357Google Scholar
  186. 186.
    Takaki K, Koshoji G, Komeyama K, Takeda M, Shishido T, Kitani A, Takehira K (2003) J Org Chem 68:6554Google Scholar
  187. 187.
    Takaki K, Komeyama K, Kobayashi D, Kawabata T, Takehira K (2006) J Alloys Compd: 408–412, 432Google Scholar
  188. 188.
    Komeyama K, Kobayashi D, Yamamoto Y, Takehira K, Takaki K (2006) Tetrahedron 62:2511Google Scholar
  189. 189.
    Mercy M, Maron L (2009) Dalton Trans:3014Google Scholar
  190. 190.
    Tani K, Kataoka Y (2001) In: Togni A, Grützmacher H (eds) Catalytic heterofunctionalization from hydroamination to hydrozirconation. Wiley, Weinheim, p 171Google Scholar
  191. 191.
    Yu X, Seo S, Marks TJ (2007) J Am Chem Soc 129:7244Google Scholar
  192. 192.
    Seo S, Yu X, Marks TJ (2009) J Am Chem Soc 131:263Google Scholar
  193. 193.
    Dzudza A, Marks TJ (2009) Org Lett 11:1523Google Scholar
  194. 194.
    Haber S, Regitz M (1997) In: de Meijere A (ed) Houben-Weyl methods of organic chemistry, vol 17f. Thieme, New York, p 1051Google Scholar
  195. 195.
    Thompson ME, Baxter SM, Bulls AR, Burger BJ, Nolan MC, Santarsiero BD, Schaefer WP, Bercaw JE (1987) J Am Chem Soc 109:203Google Scholar
  196. 196.
    St. Clair M, Schaefer WP, Bercaw JE (1991) Organometallics 10:525Google Scholar
  197. 197.
    Den Haan KH, Wielstra Y, Teuben JH (1987) Organometallics 6:2053Google Scholar
  198. 198.
    Heeres HJ, Nijhoff J, Teuben JH, Rogers RD (1993) Organometallics 12:2609Google Scholar
  199. 199.
    Evans WJ, Keyer RA, Ziller JW (1993) Organometallics 12:2618Google Scholar
  200. 200.
    Schaverien CJ (1994) Organometallics 13:69Google Scholar
  201. 201.
    Duchateau R, van Wee CT, Teuben JH (1996) Organometallics 15:2291Google Scholar
  202. 202.
    Ge S, Meetsma A, Hessen B (2009) Organometallics 28:719Google Scholar
  203. 203.
    Nishiura M, Hou Z, Wakatsuki Y, Yamaki T, Miyamoto T (2003) J Am Chem Soc 125:1184Google Scholar
  204. 204.
    Kretschmer WP, Troyanov SI, Meetsma A, Hessen B, Teuben JH (1998) Organometallics 17:284Google Scholar
  205. 205.
    Tazelaar CGJ, Bambirra S, van Leusen D, Meetsma A, Hessen B, Teuben JH (2004) Organometallics 23:936Google Scholar
  206. 206.
    Komeyama K, Kawabata T, Takehira K, Takaki K (2005) J Org Chem 70:7260Google Scholar
  207. 207.
    Piers WE, Shapiro PJ, Bunel EE, Bercaw JE (1990) Synlett:74Google Scholar
  208. 208.
    Hajela S, Bercaw JE (1994) Organometallics 13:1147Google Scholar
  209. 209.
    Bercaw JE (1990) Pure Appl Chem 62:1151Google Scholar
  210. 210.
    Crabtree RH (2004) J Organomet Chem 689:4083Google Scholar
  211. 211.
    Sakaki S (2005) Top Organomet Chem 12:31Google Scholar
  212. 212.
    Watson PL (1983) J Am Chem Soc 105:6491Google Scholar
  213. 213.
    Watson PL (1983) J Chem Soc Chem Commun:276Google Scholar
  214. 214.
    Fendrick CM, Marks TJ (1986) J Am Chem Soc 108:425Google Scholar
  215. 215.
    Sherer EC, Cramer CJ (2003) Organometallics 22:1682Google Scholar
  216. 216.
    Woodrum NL, Cramer CJ (2006) Organometallics 25:68Google Scholar
  217. 217.
    Lewin JL, Woodrum NL, Cramer CJ (2006) Organometallics 25:5906Google Scholar
  218. 218.
    Sadow AD, Tilley TD (2003) Angew Chem Int Ed 42:803Google Scholar
  219. 219.
    Sadow AD, Tilley TD (2003) J Am Chem Soc 125:7971Google Scholar
  220. 220.
    Barros N, Eisenstein O, Maron L, Tilley TD (2006) Organometallics 25:5699Google Scholar
  221. 221.
    Barros N, Eisenstein O, Maron L, Tilley TD (2008) Organometallics 27:2252Google Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2010

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical Biology, RutgersThe State University of New JerseyPiscatawayUSA

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