Ti/Pd bimetallic systems for the efficient allylation of carbonyl compounds and homocoupling reactions

Chemistry - A European Journal

Volumn 17, Issue 14, 2011, Pages 3985-3994

  Millán, Alba ^a   Campaña, Araceli G ^a   Bazdi, Btissam ^a   Miguel, Delia ^a   Álvarez De Cienfuegos, Luis ^a   Echavarren, Antonio M ^b   Cuerva, Juan M ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b INSTITUTE OF CHEMICAL RESEARCH OF CATALONIA ICIQ   (Spain)

Author keywords

allylation; palladium; synthetic methods; titanium; W rtz reaction

Indexed keywords

CARBONATES; CARBOXYLATION; KETONES; PALLADIUM; TITANIUM;

ALLYL CARBONATES; ALLYLIC CARBONATES; BIMETALLIC SYSTEMS; CATALYTIC SYSTEM; CYCLIC PRODUCTS; HOMOCOUPLING REACTIONS; PRENYLATION; SYNTHETIC METHODS;

ALLYLATION;

EID: 79952830123     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201003315     Document Type: Article

References (133)

1. Selected reviews
2. Y. Yamamoto, N. Asao, Chem. Rev. 1993, 93, 2207-2293
3. C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316
4. B. W. Gung, Org. React. 2004, 64, 1-112
5. Z. Lu, S. Ma, Angew. Chem. 2008, 120, 264-303
6. Angew. Chem. Int. Ed. 2008, 47, 258-297
7. L. F. Tietze, T. Kinzel, C. C. Brazel, Acc. Chem. Res. 2009, 42, 367-378.
8. P. Barbier, C. R. Hebd. Seances Acad. Sci. 1899, 128, 110.
9. J. A. Marshall, Chem. Rev. 2000, 100, 3163-3185.
10. Zn and B
11. J. P. Takahara, Y. Masuyama, Y. Kurusu, J. Am. Chem. Soc. 1992, 114, 2577-2586
12. S. Sebelius, O. A. Wallner, K. J. Szabó, Org. Lett. 2003, 5, 3065-3068
13. S.-F. Zhu, Y. Yang, L.-X. Wang, B. Liu, Q.-L. Zhou, Org. Lett. 2005, 7, 2333-2335.
14. Pd and Sn
15. Y. Masuyama, N. Kinugawa, Y. Kurusu, J. Org. Chem. 1987, 52, 3702-3704
16. W. Qui, Z. Wang, J. Chem. Soc. Chem. Commun. 1989, 356-357.
17. II:, T. Tabuchi, J. Inanaga, M. Yamaguchi, Tetrahedron Lett. 1986, 27, 1195-1196.
18. Rh:, M. Vasylyev, H. Alper, J. Org. Chem. 2010, 75, 2710-2713.
19. The group of Krische reported new allylations that use iridium complexes and a source of hydrogen but the procedure seems to be limited to simple allyl and α-methyl allyl acetate as pro-nucleophiles and aldehydes as electrophiles
20. I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2008, 130, 14891-14899
21. I. S. Kim, M.-Y. Ngai, M. J. Krische, J. Am. Chem. Soc. 2009, 131, 2514-2520
22. S. B. Han, H. Han, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 1760-1761
23. Y. J. Zhang, J. H. Yang, S. H. Kim, M. J. Krische, J. Am. Chem. Soc. 2010, 132, 4562-4563.
24. R. E. Taylor, J. P. Ciavarri, Org. Lett. 1999, 1, 467-469.
25. W. Qiu, Z. Wang, J. Chem. Soc. Chem. Commun. 1989, 356-357
26. J. P. Takahara, Y. Masuyama, Y. Kurusu, J. Am. Chem. Soc. 1992, 114, 2577-2586
27. H. Nakamura, N. Asao, Y. Yamamoto, J. Chem. Soc. Chem. Commun. 1995, 1273-1274.
28. A. G. Campaña, B. Bazdi, N. Fuentes, R. Robles, J. M. Cuerva, J. E. Oltra, S. Porcel, A. M. Echavarren, Angew. Chem. 2008, 120, 7625-7629
29. Angew. Chem. Int. Ed. 2008, 47, 7515-7519.
30. III-mediated Barbier-type reactions from allylic halide starting materials with a regioselectivity which diverges from the NHK reaction
31. A. Rosales, J. L. Oller-Lopez, J. Justicia, A. Gansäuer, J. E. Oltra, J. M. Cuerva, Chem. Commun. 2004, 2628-2629
32. R. E. Estévez, J. Justicia, B. Bazdi, N. Fuentes, M. Paradas, D. Choquesillo-Lazarte, J. M. García-Ruiz, R. Robles, A. Gansäuer, J. M. Cuerva, J. E. Oltra, Chem. Eur. J. 2009, 15, 2774-2791
33. J. Justicia, I. Sancho-Sanz, E. Alvarez-Manzaneda, J. E. Oltra, J. M. Cuerva, Adv. Synth. Catal. 2009, 351, 2295-2300
34. J. E. Oltra, J. M. Cuerva, Adv. Synth. Catal. 2009, 351, 2295-2300.
35. For seminal works in titanocene(III) chemistry, see
36. T. V. RajanBabu, W. A. Nugent, J. Am. Chem. Soc. 1994, 116, 986-997
37. A. Gansäuer, H. Bluhm, M. Pierobon, J. Am. Chem. Soc. 1998, 120, 12849-12859.
38. For recent reviews, see
39. A. Gansäuer, T. Lauterbach, S. Narayan, Angew. Chem. 2003, 115, 5714-5731
40. Angew. Chem. Int. Ed. 2003, 42, 5556-5573
41. J. M. Cuerva, J. Justicia, J. L. Oller-López, J. E. Oltra, Top. Curr. Chem. 2006, 264, 63-91.
42. J. Justicia, A. Rosales, E. Buñuel, J. L. Oller-López, M. Valdivia, A. Haídour, A.; J. E. Oltra, A. F. Barrero, D. J. Cárdenas, J. M. Cuerva, Chem. Eur. J. 2004, 10, 1778-1788
43. J. E. Oltra, A. F. Barrero, D. J. Cárdenas, J. M. Cuerva, Chem. Eur. J. 2004, 10, 1778-1788
44. J. Justicia, J. L. Oller-López, A. G. Campaña, J. E. Oltra, J. M. Cuerva, E. Buñuel, D. J. Cárdenas, J. Am. Chem. Soc. 2005, 127, 14911-14921
45. J. M. Cuerva, A. G. Campaña, J. L. Oller-López, J. Justicia, A. Rosales, R. Robles, E. Buñuel, D. J. Cárdenas, J. E. Oltra, Angew. Chem. 2006, 118, 5648-5652
46. Angew. Chem. Int. Ed. 2006, 45, 5522-5526
47. R. E. Estévez, J. L. Oller-López, R. Robles, C. R. Melgarejo, A. Gansäuer, J. M. Cuerva, J. E. Oltra, Org. Lett. 2006, 8, 5433-5436.
48. For a review of the advantages of these mixed systems, see:, L. Ford, U. Jahn, Angew. Chem. 2009, 121, 6504-6507
49. Angew. Chem. Int. Ed. 2009, 48, 6386-6389.
50. For selected references of closely related nucleophiles
51. A. Kasatkin, T. Nakagawa, S. Okamoto, F. Sato, J. Am. Chem. Soc. 1995, 117, 3881-3882
52. F. Sato, S. Iijima, M. Sato, Tetrahedron Lett. 1981, 22, 243-246.
53. 2]; see
54. R. J. EnemÃ∥rke, J. Larsen, T. Skrydstrup, K. Daasbjerg, J. Am. Chem. Soc. 2004, 126, 7853-7864
55. K. Daasbjerg, H. Svith, S. Grimme, M. Gerenkamp, C. Mück- Lichtenfeld, A. Gansäuer, A. Barchuck, F. Keller, Angew. Chem. 2006, 118, 2095-2098
56. Angew. Chem. Int. Ed. 2006, 45, 2041-2044
57. 2TiCl].
58. For a review, see: D. C. Billington, in Comprehensive Organic Synthesis Ed. B. M. Trost, I. Fleming, Chapter 2.1, Vol. 3, Pergamon Press, Oxford, 1991. For a selected reference in the field of natural product synthesis
59. N. H. Chishti, S. M. Coppell, R. Ramage, Tetrahedron Lett. 1975, 16, 1025.
60. G. W. Ebert, R. D. Rieke, J. Org. Chem. 1988, 53, 4482-4488
61. F. O. Ginah, T. A. Donovan, Jr., S. D. Suchan, D. R. Pfennig, G. W. Ebert, J. Org. Chem. 1990, 55, 584
62. J. Ma, T.-H. Chan, Tetrahedron Lett. 1998, 39, 2499.
63. P. Girard, J. L. Namy, H. B. Kagan, J. Am. Chem. Soc. 1980, 102, 2693-2698
64. Cr. Y. Okude, T. Hiyama, H. Nozaki, Tetrahedron Lett. 1977, 18, 3829-3830.
65. A. F. Barrero, M. M. Herrador, J. F. Quilez del Moral, P. Arteaga, J. F. Arteaga, M. Piedra, E. M. Sanchez, Org. Lett. 2005, 7, 2301-2304.
66. D. H. Hill, M. A. Parvez, A. Sen, J. Am. Chem. Soc. 1994, 116, 2889-2901.
67. W. G. Dauben, G. H. Beasly, M. D. Broadhurst, B. Muller, D. J. Peppard, P. Pesnelle, C. Suter, J. Am. Chem. Soc. 1974, 96, 4724-4726
68. E. J. Corey, J. Am. Chem. Soc. 1972, 94, 667-668
69. E. J. Corey, E. Hamanaka, J. Am. Chem. Soc. 1967, 89, 2758-2759
70. E. J. Corey, E. A. Broger, Tetrahedron Lett. 1969, 10, 1779-1782.
71. For other Würtz-type couplings of allylic carboxylates, see
72. B. M. Trost, K. M. Pietrusiewicz, Tetrahedron Lett. 1985, 26, 4039
73. S.-I. Sasaoka, T. Yamamoto, H. Kinoshita, K. Inomata, H. Kotake, Chem. Lett. 1985, 315-318
74. Y. Masuyama, K. Otake, Y. Kurusu, Bull. Chem. Soc. Jpn. 1987, 60, 1527-1528.
75. For recent reviews, see
76. A. Gansäuer, B. Rinker, in Titanium and Zirconium in Organic Synthesis (Ed.:, I. Marek,), Wiley-VCH, Weinheim, Germany, 2002, pp. 435-450
77. A. Gansäuer, S. Narayan, Adv. Synth. Catal. 2002, 344, 465-475
78. A. Gansäuer, B. Rinker, Tetrahedron 2002, 58, 7017-7026
79. A. Gansäuer, M. Pierobon, in Radicals in Organic Synthesis, Vol. 2 (Eds.:, P. Renaud, M. P. Sibi,), Wiley-VCH, Weinheim, Germany, 2001, pp. 207-220
80. A. Gansäuer, H. Bluhm, Chem. Rev. 2000, 100, 2771-2788.
81. A. Gansäuer, M. Pierobon, H. Bluhm, Angew. Chem. 1998, 110, 107-109
82. Angew. Chem. Int. Ed. 1998, 37, 101-103
83. A. Gansäuer, H. Bluhm, Chem. Commun. 1998, 2143-2144
84. S. Fuse, M. Hanochi, T. Doi, T. Takahashi, Tetrahedron Lett. 2004, 45, 1961.
85. A. F. Barrero, A. Rosales, J. M. Cuerva, J. E. Oltra, Org. Lett. 2003, 5, 1935- 1938.
86. 2] catalyst was also able to carry out the reaction but with lower yield and stereoselectivities.
87. We have only detected the I-coupling product in trace amounts
88. J. Justicia, J. E. Oltra, J. M. Cuerva, J. Org. Chem. 2004, 69, 5803-5806
89. A. M. Castaño, A. M. Echavarren, Tetrahedron Lett. 1996, 37, 6587
90. A. M. Castaño, M. Mendez, M. Ruano, A. M. Echavarren, J. Org. Chem. 2001, 66, 589.
91. M. Paradas, A. G. Campaña, T. Jiménez, R. Robles, J. E. Oltra, E. Buñuel, J. Justicia, D. J. Cardenas, J. M. Cuerva, J. Am. Chem. Soc. 2010, 132, 12748-12756.
92. D. J. Porter, F. L. Boyd, J. Biol. Chem. 1992, 267, 3205-3213
93. K. H. Gardner, L. E. Kay, J. Am. Chem. Soc. 1997, 119, 7599-7600
94. T. Junk, W. J. Catallo, Chem. Soc. Rev. 1997, 26, 401-406
95. H. Nakazawa, S. Ino, K. Kato, T. Watanabe, Y. Ito, H. Oka, J. Chromatogr. B: Biomed Sci. Appl. 1999, 732, 55-64
96. D. M. Marcus, M. J. Hayman, Y. M. Blau, D. R. Guenther, J. O. Ehresmann, P. W. Kletnieks, J. F. Haw, Angew. Chem. 2006, 118, 1967-1969
97. Angew. Chem. Int. Ed. 2006, 45, 1933-1935
98. J. Atzrodt, V. Derdau, T. Fey, J. Zimmermann, Angew. Chem. 2007, 119, 7890-7911
99. Angew. Chem. Int. Ed. 2007, 46, 7744-7765.
100. R. A. Rudel, D. E. Camann, J. D. Spengler, L. R. Korn, J. G. Brody, Environ. Sci. Technol. 2003, 37, 4543-4553
101. E. Stokvis, H. Rosing, J. H. Beijnen, Rapid Commun. Mass Spectrom. 2005, 19, 401-407
102. Y. Suzuki, T. Korenaga, Y. Chikaraishi, Chem. Lett. 2006, 35, 532-533.
103. A proof of principle of such an analysis used deuterated products, derived from titanocene(III)-mediated deuterations:, T. Jiménez, A. G. Campaña, B. Bazdi, M. Paradas, D. Arráez-Román, A. Segura-Carretero, A. Fernández-Gutiérrez, J. E. Oltra, R. Robles, J. Justicia, J. M. Cuerva, Eur. J. Org. Chem. 2010, 4288-4295.
104. Although the reason is not clear without considering the electronic effects, it is known that phosphites are in some cases unstable in the presence of radicals:, M. Bietti, A. Calcagni, M. Salamone, J. Org. Chem. 2010, 75, 4514-4520.
105. II chemistry is the high atomic weight of Sm, which requires the use of a large amount of reagent with respect to the organic substrate-moreover, Sm is a relatively expensive metal
106. H. B. Kagan, Tetrahedron 2003, 59, 10351-10372; recently a catalytic version in Sm has been described but with limited success
107. S. Médégan, F. Hélion, J.-L. Namy, Eur. J. Org. Chem. 2005, 4715-4722.
108. F. Sato, S. Iijima, M. Sato, Tetrahedron Lett. 1981, 22, 243-246
109. F. Sato, K. Iida, S. Iijima, H. Moriya, M. Sato, J. Chem. Soc. Chem. Commun. 1981, 1140-1141
110. F. Sato, H. Uchiyama, K. Iida, Y. Kobayashi, M. Sato, J. Chem. Soc. Chem. Commun. 1983, 921-922.
111. 0-active species from the palladium(II) pre-catalyst is required.
112. 2 has been described:, R. S. P. Coutts, P. C. Wailes, R. L. Martin, J. Organomet. Chem. 1973, 47, 375-382.
113. M. Paradas, A. G. Campaña, R. E. Estévez, L. Álvarez de Cienfuegos, T. Jiménez, R. Robles, J. M. Cuerva, J. E. Oltra, J. Org. Chem. 2009, 74, 3616-3619.
114. A. Fernandez-Mateos, P. Herrero-Teijoón, L. Mateo Burón, R. Rabanedo-Clemente, R. Rubio-Gonzalez, J. Org. Chem. 2007, 72, 9973-9982.
115. 3-allyl)palladium complexes derived from a transmetallation step between species II and IV could also explain the experimental results:, H. Nakamura, H. Iwama, Y. Yamamoto, J. Am. Chem. Soc. 1996, 118, 6641-6647.
116. 1-Allylpalladium complexes
117. O. A. Wallner, K. J. Szabó, J. Org. Chem. 2003, 68, 2934-2943
118. N. Solin, J. Kjellgren, K. Szabo, J. Am. Chem. Soc. 2004, 126, 7026-7033
119. K. J. Szabó, Chem. Eur. J. 2004, 10, 5268-5275.
120. A. Yanagisawa, H. Hibino, S. Habaue, Y. Hisada, H. Yamamoto, J. Org. Chem. 1992, 57, 6386-6389.
121. W. v. E. Doering, L. Birladeanu, K. Sarma, J. H. Teles, F.-G. Klärner, J.-S. Gehrke, J. Am. Chem. Soc. 1994, 116, 4289-4297.
122. C. K. Lau, C. Dufresne, P. C. Bélanger, S. Piètrè, J. Scheigetz, J. Org. Chem. 1986, 51, 3038-3043.
123. A. Dommisse, J. Wirtz, K. Koch, W. Barthlott, J. Kolter, Eur. J. Org. Chem. 2007, 3508-3511.
124. S. Kobayashi, K. Nishio, J. Org. Chem. 1994, 59, 6620-6628.
125. R. Guyon, P. Villa, Bull. Soc. Chim. Fr. 1972, 1375-1384.
126. S. Casolari, D. D′Addario, E. Tagliavini, Org. Lett. 1999, 1, 1061-1063.
127. J. G. Kim, K. W. Waltz, I. F. García, D. Kwiatkowski, J. P. Walsh, J. Am. Chem. Soc. 2004, 126, 12580-12585.
128. S. J. Jong, J. M. Fang, J. Org. Chem. 2001, 66, 3533-3537.
129. L. Zhao, D. J. Burnell, Tetrahedron Lett. 2006, 47, 3291-3294.
130. L. A. Paquette, P. C. Lobben, J. Org. Chem. 1998, 63, 5604-5616.
131. S.-I. Sumida, M. Ohga, J. Mitani, J. Nokami, J. Am. Chem. Soc. 2000, 122, 1310-1313.
132. D. Furlani, D. Marton, G. Taglianni, M. Zordan, J. Organomet. Chem. 1988, 341, 345-346.
133. R. Wada, K. Oisaki, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2004, 126, 8910-8911.