A resourceful new strategy in organic synthesis: Tandem and stepwise metathesis/non-metathesis catalytic processes

Journal of Organometallic Chemistry

Volumn 691, Issue 24-25, 2006, Pages 5129-5147

  Dragutan, Valerian ^a   Dragutan, Ileana ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Romania)

Author keywords

Catalysis; Metal alkylidenes; Metathesis; Non metathetical processes; Tandem; Transition metals

Indexed keywords

CATALYSIS; HYDROGENATION; ISOMERIZATION; OXIDATION; REACTION KINETICS; SYNTHESIS (CHEMICAL);

ALLYLATION; METAL-ALKYLIDENES; NON-METATHETICAL PROCESSES; TANDEM METATHESIS;

ORGANIC COMPOUNDS;

BETULACEAE;

EID: 33751236180     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2006.08.012     Document Type: Article

References (168)

1. Crabtree R.H. The Organometallic Chemistry of the Transition Metals (1988), Wiley, New York
2. Throughout the review the concept "Tandem" has been used according to the following wide acceptance: one behind another, alongside each other, and an association of events working towards the same goal. "Tandem reactions" = multiple reactions combined in one synthetic operation without isolating intermediates [2b]. "Tandem catalysis" = strategy involving sequential catalytic reactions with minimum change of conditions [2c]. Since this work reviews metathetical and non-metathetical processes, the described coupled reactions are a priori mechanistically distinct [2e]
3. Ho T.-L. Tandem Organic Reactions (1992), Wiley-Interscience, New York
4. Wasilke J.-C., Obrey S.J., Baker R.T., and Bazan G.C. Chem. Rev. 105 (2005) 1001
5. De Meijere A., von Zezschwitz P., and Brase S. Acc. Chem. Res. 38 (2005) 413
6. Fogg D., and dos Santos E.N. Coord. Chem. Rev. 248 (2004) 2365
7. Tietze L.F. Chem. Rev. 96 (1996) 115
8. Denmark S.E., and Thorarensen A. Chem. Rev. 96 (1996) 137
9. Posner G.H. Chem. Rev. 86 (1986) 831
10. Tietze L.F., and Beifuss U. Angew. Chem., Int. Ed. 32 (1993) 131
11. Nicolaou K.C., Bulger P.G., and Sarlach D. Angew. Chem., Int. Ed. 44 (2005) 4490
12. Hall N. Science 266 (1994) 32
13. La D.S., Ford J.G., Sattely E.S., Bonitatebus P.J., Schrock R.R., and Hoveyda A.H. J. Am. Chem. Soc. 121 (1999) 11603
14. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413
15. Randall M.L., and Snapper M.L. J. Mol. Catal. A 133 (1998) 29
16. Diver S.T., and Giessert A.J. Chem. Rev. 104 (2004) 1317
17. Schmidt B. Pure Appl. Chem. 78 (2006) 469
18. Schmidt B. Angew. Chem., Int. Ed. 42 (2003) 4996
19. Schmidt B. Eur. J. Org. Chem. (2004) 1865
20. Vaillard S.E., Postigo A., and Rossi R.A. J. Org. Chem. 67 (2002) 8500
21. Donohoe T.J., Orr A.J., and Bingham M. Angew. Chem., Int. Ed. 45 (2006) 2664
22. Boyer F.D., and Hanna I. Eur. J. Org. Chem. (2006) 471
23. Cossy J., Bargiggia F.C., and BouzBouz S. Tetrahedron Lett. 43 (2002) 6715;
24. In: Grubbs R.H. (Ed). Handbook of Metathesis (2003), Wiley-VCH, Weinheim
25. Schrock R.R. Angew. Chem., Int. Ed. 118 (2006) 3832
26. Schrock R.R. Chem. Rev. 102 (2002) 145
27. Grubbs R.H. Angew. Chem., Int. Ed. 118 (2006) 3845
28. Fürstner A. Angew. Chem., Int. Ed. 39 (2000) 3012
29. Buchmeiser M.R. Chem. Rev. 100 (2000) 1565
30. Bourissou D., Guerret O., Gabai F.P., and Bertrand G. Chem. Rev. 100 (2000) 39
31. Diez-Gonzalez S., and Nolan S.P. Ann. Rep. Progr. Chem. Sect. B 101 (2005) 171
32. Cardin D.J., Cetinkaya B., and Lappert M.F. Chem. Rev. 72 (1972) 545
33. Lappert M.F. J. Organomet. Chem. 690 (2005) 5467
34. Crabtree R.H. J. Organomet. Chem. 690 (2005) 5451
35. Herrmann W.A., Weskamp T., and Böhm V.P.W. Adv. Organomet. Chem. 48 (2001) 1
36. Alcaide B., and Almendros P. Chem. Eur. J. 9 (2003) 1259
37. V. Dragutan, I. Dragutan, L. Delaude, A. Demonceau, Coord. Chem. Rev. (2006) in press (special issue Carbene Chemistry.
38. Drouin S.D., Zamanian F., and Fogg D.E. Organometallics 20 (2001) 5495
39. Fogg D.E., Amoroso D., Drouin S.D., Snelgrove J., Conrad J., and Zamanian F. J. Mol. Catal. A 190 (2002) 177
40. Cadot C., Dalko P.I., and Cossy J. Tetrahedron Lett. 43 (2002) 1839
41. Alcaide B., Almendros P., and Alonso J.M. Chem. Eur. J. 9 (2003) 5793
42. Quayle P., Fengas D., and Richards S. Synlett (2003) 1797
43. Maifeld S.V., Miller R.L., and Lee D. Tetrahedron Lett. 43 (2002) 6363
44. Maifeld S.V., Tran M.N., and Lee D. Tetrahedron Lett. 46 (2005) 105
45. Simal F., Democeau A., and Noels A.F. Tetrahedron Lett. 40 (1999) 5689
46. De Clercq B., and Verpoort F. Tetrahedron Lett. 42 (2001) 8959
47. Drozdzak R., Allaert B., Ledoux N., Dragutan I., Dragutan V., and Verpoort F. Adv. Synth. Catal. 347 (2005) 1721
48. De Clercq B., and Verpoort F. Macromolecules 35 (2002) 8943
49. De Clercq B., and Verpoort F. Polym. Bull. 50 (2003) 153
50. Drozdzak R., Allaert B., Ledoux N., Dragutan I., Dragutan V., and Verpoort F. Coord. Chem. Rev. 249 (2005) 3055
51. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46
52. Trost B.M., Frederiksen M.U., and Rudd M.T. Angew. Chem., Int. Ed. 44 (2005) 6630
53. Ajamian A., and Gleason J.L. Angew. Chem., Int. Ed. 43 (2004) 3754
54. Furstner A., and Leitner A. Angew. Chem., Int. Ed. 42 (2003) 308
55. Schrock R.R., Murdzek J.S., Bazan G.C., Robbins J., DiMare M., and O'Regan M. J. Am. Chem. Soc. 112 (1990) 3875
56. Weatherhead G.S., Ford J.G., Alexanian E.J., Schrock R.R., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 1828
57. Fu G.C., Nguyen S.T., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 115 (1993) 9856
58. Trnka T.M., and Grubbs R.H. Acc. Chem. Res. 34 (2001) 18
59. Ivin K.J., and Mol J.C. Olefin Metathesis and Metathesis Polymerization (1997), Academic Press, London
60. In: Furstner A. (Ed). Alkene Metathesis in Organic Synthesis (1998), Springer, Berlin
61. In: Bruneau C., and Dixneuf P.H. (Eds). Ruthenium Catalysts and Fine Chemistry (2004), Springer, Berlin
62. Schrock R.R., and Hoveyda A.H. Angew. Chem., Int. Ed. 42 (2003) 4592
63. Schrock R.R. Chem. Commun. (2005) 2773
64. Schrock R.R. Top. Organomet. Chem. 1 (1998) 1
65. Nguyen S.T., Johnson L.K., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 114 (1992) 3974
66. Nguyen S.T., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 115 (1993) 9858
67. Schwab Pi., Grubbs R.H., and Ziller J.W. J. Am. Chem. Soc. 118 (1996) 100
68. Huang J., Stevens E.D., Nolan S.P., and Petersen J.L. J. Am. Chem. Soc. 121 (1999) 2674
69. Huang J., Schanz H.-J., Stevens E.D., and Nolan S.P. Organometallics 18 (1999) 2370
70. Scholl M., Trnka T.M., Morgan J.P., and Grubbs R.H. Tetrahedron Lett. 40 (1999) 2247
71. Scholl M., Ding S., Lee G.W., and Grubbs R.H. Org. Lett. 1 (1999) 953
72. Weskamp T., Kohl F.J., Hieringer W., Gleich D., and Herrmann W.A. Angew. Chem., Int. Ed. 38 (1999) 2416
73. Choi T.L., Chatterjee A.K., and Grubbs R.H. Angew. Chem., Int. Ed. 40 (2001) 1277
74. Garber S.B., Kingsbury J.S., Gray B.L., and Hoveyda A.H. J. Am. Chem. Soc. 122 (2000) 8168
75. Love J.A., Morgan J.P., Trnka T.M., and Grubbs R.H. Angew. Chem., Int. Ed. 41 (2002) 4035
76. Drozdzak R., Ledoux N., Allaert B., Dragutan I., Dragutan V., and Verpoort F. Cent. Eur. J. Chem. 3 (2005) 404
77. McLain S.J., McCord E.F., Arthur S.D., Hauptman A.E., Feldman J., Nugent W.A., Johnson L.K., Mecking S., and Brookhart M. Proc. Am. Chem. Soc.: Div. Polym. Mater. Sci. Eng. 76 (1997) 246
78. Dias E.L., and Grubbs R.H. Organometallics 17 (1998) 2758
79. Bielawski C.W., Louie J., and Grubbs R.H. J. Am. Chem. Soc. 122 (2000) 12872
80. Drouin S.D., Yap G.P.A., and Fogg D.E. Inorg. Chem. 39 (2000) 5412
81. Cobo N., Esteruelas M.A., González F., Herrero J., López A.M., Lucio P., and Oliván M. J. Catal. 223 (2004) 319
82. Watson M.D., and Wagener K.B. Macromolecules 33 (2000) 3196
83. Bielawski C.W., and Grubbs R.H. Angew. Chem., Int. Ed. 39 (2000) 2903
84. Louie J., Bielawski C.W., and Grubbs R.H. J. Am. Chem. Soc. 123 (2001) 11312
85. Fürstner A., and Leitner A. Angew. Chem., Int. Ed. 42 (2003) 308
86. Børsting P., and Nielsen P. Chem. Commun. (2002) 2140
87. Børsting P., and Nielsen P. Nucleosides Nucleotides Nucleic Acids 22 (2003) 1139
88. Schmidt B., and Pohler M. Org. Biomol. Chem. 1 (2003) 2512
89. Whelan A.N., Elaridi J., Harte M., Smith S.V., Jackson V.R., and Robinson A.J. Tetrahedron Lett. 45 (2004) 9545
90. Whelan A.N., Elaridi J., Mulder R.J., Robinson A.J., and Jackson W.R. Can. J. Chem. 83 (2005) 875
91. Cossy J., Bargiggia F.C., and BouzBouz S. Org. Lett. 5 (2003) 459
92. Kamimura A., Tanaka K., Hayashi T., and Omata Y. Tetrahedron Lett. 47 (2006) 3625
93. Randl S., and Blechert S. J. Org. Chem. 68 (2003) 8879
94. Burnett R.L., and Hughes T.R. J. Catal. 31 (1973) 55
95. Basset J.M., Copéret C., Lefort L., Maunders B.M., Maury O., Le Roux E., Saggio G., Soignier S., Soulivong D., Sunley G.J., Taoufik M., and Thivolle-Cazat J. J. Am. Chem. Soc. 127 (2005) 8604
96. Goldman A.S., Roy A.H., Huang Z., Ahuja R., Schinski W., and Brookhart N. Science 312 (2006) 257
97. Dieltiens N., Stevens C.V., De Vos D., Allaert B., Drozdzak R., and Verpoort F. Tetrahedron Lett. 45 (2004) 8995
98. Moonen K., Dieltiens N., and Stevens C.V. J. Org. Chem. 71 (2006) 4006
99. van Otterlo W.A.L., Coyanis E.M., Panayides J.-L., De Koning C.B., and Fernandes M.A. Synlett (2005) 501
100. Statsuk A.V., Liu D., and Kozmin S.A. J. Am. Chem. Soc. 126 (2004) 9546
101. Sutton A.E., Seigal B.A., Finnegan D.F., and Snapper M.L. J. Am. Chem. Soc. 124 (2002) 3390;
102. Schmidt B. Chem. Commun. (2004) 742
103. Schmidt B. J. Org. Chem. 69 (2004) 7672
104. B. Schmidt, in: Proceeding of the 16th International Symposium on Olefin Metathesis and Related Reactions, August 7-12, 2005, Poznan, Poland, SL6.
105. Schmidt B. J. Mol. Catal. A 254 (2006) 53
106. Chiu P.L., and Lee H.M. Organometallics 24 (2005) 1692
107. Fustero S., Sánchez-Roselló M., Jiménez D., Sanz-Cervera J.F., del Pozo C., and Aceña J.L. J. Org. Chem. 71 (2006) 2706
108. Michalak M., and Wicha J. Synlett (2005) 2277
109. van Otterlo W.A.L., Ngidi E.L., and de Koning C.B. Tetrahedron Lett. 44 (2003) 6483
110. van Otterlo W.A.L., Morgans G.L., Khanye S.D., Aderibigbe B.A.A., Michael J.P., and Billing D.G. Tetrahedron Lett. 45 (2004) 9171
111. van Otterlo W.A.L., Morgans G.L., Madeley L.G., Kuzvidza S., Moleele S.S., Thornton N., and de Koning C.B. Tetrahedron 61 (2005) 7746
112. Braddock D.C., and Matsuno A. Tetrahedron Lett. 43 (2002) 3305
113. Braddock D.C., and Wildsmith A.J. Tetrahedron Lett. 42 (2001) 3239
114. Tissot-Croset K., Polet D., Gille S., Hawner C., and Alexakis A. Synthesis (2004) 2586
115. Arisawa M., Theeraladanon C., Nishida A., and Nakagawa M. Tetrahedron Lett. 42 (2001) 8029
116. Okada A., Ohshima T., and Shibasaki M. Tetrahedron Lett. 42 (2001) 8023
117. Lee C.-H.A., and Loh T.-P. Tetrahedron Lett. 47 (2006) 809
118. Hoffmann R.W. Pure Appl. Chem. 60 (1988) 123
119. Roush W.R., Ando K., Powers D.B., Palkowitz A.D., and Halterman R.L. J. Am. Chem. Soc. 112 (1990) 6339
120. Brown H.C., Racherla U.S., and Pellechia P.J. J. Org. Chem. 55 (1990) 1868
121. Goldberg S.D., and Grubbs R.H. Angew. Chem., Int. Ed. 41 (2002)
122. Nieczypor P., Mol J.C., Bespalova N.B., and Bubnov Y.N. Eur. J. Org. Chem. (2004) 812
123. Beligny S., Eibauer S., Maechling S., and Blechert S. Angew. Chem., Int. Ed. 45 (2006) 1900
124. Roth S., Göhler S., Cheng H., and Stark C.B.W. Eur. J. Org. Chem. (2005) 4109
125. Braddock D.C., Cansell G., Hermitage S.A., and White A.J.P. Tetrahedron: Asymmetry 15 (2004) 3123
126. Kim B.G., and Snapper M.L. J. Am. Chem. Soc. 128 (2006) 52
127. Poulsen C.S., and Madsen R. Synthesis (2003) 1
128. Bentz D., and Laschat S. Synthesis (2000) 1766
129. Schurer S.C., and Blechert S. Tetrahedron Lett. 40 (1999) 1877
130. Heerding D.A., Takata D.T., Kwon C., Huffman W.F., and Samanen J. Tetrahedron Lett. 39 (1998) 6815
131. Rosillo M., Casarrubios L., Dominguez G., and Pérez-Castells J. Tetrahedron Lett. 42 (2001) 7029
132. Rosillo M., Domi'nguez G., Casarrubios L., Amador U., and Pérez-Castells J. J. Org. Chem 69 (2004) 2084
133. Moreno-Mañas M., Pleixats R., and Santamaria A. Synlett (2001) 1784
134. Duboc R., Henaut C., Sovignac M., Genet J.-P., and Bhatnagar N. Tetrahedron Lett. 42 (2001) 2464
135. Renaud J., Graf C.-D., and Oberer L. Angew. Chem. Int. Ed. 39 (2000) 3101
136. Majumdar K.C., Rahaman H., Muhuri S., and Roy B. Synlett (2006) 466
137. Banti D., and North M. Adv. Synth. Catal. 344 (2002) 694
138. Majumdar K.C., Rahaman H., Islam R., and Roy B. Tetrahedron Lett. 47 (2006) 2111
139. Chattopadhyay S.K., Maity S., and Panja S. Tetrahedron Lett. 43 (2002) 7781
140. Barrett A.G.M., Ahmed M., Baker S.P., Baugh S.P.D., Braddock D.C., Procopiou P.A., White A.J.P., and Williams D.J. J. Org. Chem. 65 (2000) 3716
141. Srikrishna A., Vasantha Lakshmi B., and Mathews M. Tetrahedron Lett. 47 (2006) 2103
142. Krafft M.E., Song E.-H., and Davoile R.J. Tetrahedron Lett. 45 (2005) 6359
143. Gowrisankar S., Lee K.Y., and Kim J.N. Tetrahedron 62 (2006) 4052
144. Banfi L., Basso A., Guanti G., and Riva R. Tetrahedron Lett. 44 (2003) 7655
145. Oikawa M., Naito S., and Sasaki M. Tetrahedron Lett. 47 (2006) 4763
146. Grigg R., Martin W., Morris J., and Sridharan V. Tetrahedron 61 (2005) 11380
147. García-Fandiño R., Aldegunde M.J., Codesido E.M., Castedo L., and Granja J.R. J. Org. Chem. 70 (2005) 8281
148. White B.H., and Snapper M.L. J. Am. Chem. Soc. 125 (2003) 14901
149. Rosillo M., Casarrubios L., Dominguez G., and Perez-Castells J. Org. Biomol. Chem. 1 (2003) 1450
150. Ortega N., Martin T., and Martin V.S. Org. Lett. 8 (2006) 871
151. Poulsen C.S., and Madsen R. J. Org. Chem. 67 (2002) 4441
152. Smith III A.B., and Kim D.-S. J. Org. Chem. 71 (2006) 2547
153. Simal F., Demonceau A., and Noels A.F. Angew. Chem., Int. Ed. 38 (1999) 538
154. Tallarico J.A., Malnick L.M., and Snapper M.L. J. Org. Chem. 64 (1999) 344
155. DeClercq B., and Verpoort F. Tetrahedron Lett. 43 (2002) 4687
156. Opstal T., and Verpoort F. Synlett 6 (2002) 935
157. Quayle P., Fengas D., and Richards S.N. Synlett (2003) 1797
158. Schmidt B., Pohler M., and Costisella B. J. Org. Chem. 69 (2004) 421
159. Seigal B.A., Fajardo C., and Snapper M.L. J. Am. Chem. Soc. 127 (2005) 16329
160. Schmidt B., and Pohler M. J. Organomet. Chem. 690 (2005) 5552
161. Faulkner J., Edlin C.D., Fengas D., Preece I., Quayle P., and Richards S.N. Tetrahedron Lett. 46 (2005) 2381
162. Edlin C.D., Faulkner J., and Quayle P. Tetrahedron Lett. 47 (2006) 1145
163. In: Matyjaszewski K., and Davis T.P. (Eds). Handbook of Radical Polymerization (2002), Wiley-Interscience, Hoboken
164. Dragutan V., and Streck R. Catalytic Polymerization of Cycloolefins (2000), Elsevier, Amsterdam
165. C.W. Bielawski, R.H. Grubbs, Polymer Preprints, Division of Polymer Chemistry, American Chemical Society, vol. 41, 2000, p. 12.
166. Bielawski C.W., Morita T., and Grubbs R.H. Macromolecules 33 (2000) 678
167. Demonceau A., Simal F., and Noels A.F. NATO Science Series, II: Mathematics, Physics and Chemistry (Ring Opening Metathesis Polymerization and Related Chemistry) vol. 56 (2002), Kluwer Academic Publishers, Dordrecht, The Netherlands 227-245
168. Mahanthappa M.K., Bates F.S., and Hillmyer M.A. Macromolecules 38 (2005) 7890