Efficient and selective telomerization of 1,3-butadiene with diols catalyzed by palladium-carbene complexes

ChemSusChem

Volumn 2, Issue 1, 2009, Pages 63-70

  Grotevendt, Anne ^a   Jackstell, Ralf ^a   Michalik, Dirk ^a   Gomez, Mario ^b   Beller, Matthias ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b Evonik Rohm GmbH   (Germany)

Author keywords

Carbenes; Homogeneous catalysis; Palladium; Telomerization

Indexed keywords

ALCOHOLS; CATALYSIS; CATALYSTS; ORGANIC COMPOUNDS; PALLADIUM; POLYMERIZATION;

CARBENES; ETHER DERIVATIVES; HOMOGENEOUS CATALYSIS; OPTIMIZED REACTION CONDITIONS; PALLADIUM CARBENE COMPLEXES; TELOMERIZATION; TURNOVER NUMBER; UNSATURATED ALCOHOLS;

PALLADIUM COMPOUNDS;

1,3 BUTADIENE; 1,3 BUTADIENE DERIVATIVE; 1,3-BUTADIENE; CARBENE; DRUG DERIVATIVE; ETHER DERIVATIVE; GLYCOL; METHANE; ORGANOMETALLIC COMPOUND; PALLADIUM; POLYMER;

ARTICLE; CATALYSIS; CHEMISTRY; ENZYME SPECIFICITY;

BUTADIENES; CATALYSIS; ETHERS; GLYCOLS; METHANE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; POLYMERS; SUBSTRATE SPECIFICITY;

EID: 60549116581     PISSN: 18645631     EISSN: 1864564X     Source Type: Journal    
DOI: 10.1002/cssc.200800162     Document Type: Article

References (122)

1. For reviews on telomerization reactions, see:
2. a) D. J. Nielsen, K.J. Cavell, N-Heterocydic Carbenes in Synthesis (Ed.: S. P. Nolan), Wiley-VCH, Weinheim, 2006, 73-100;
3. b) N. Yoshimura, Applied Homogeneous Catalysis with Organometallic Compounds, Vol. 1 (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2000, p. 361;
4. c) J. Tsuji, Palladium Reagents and Catalysts: Innovations in Organic Synthesis, John Wiley & Sons, Chichester, 1995, p. 422;
5. d) J. M. Takacs in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon Press, Oxford, 1995, p. 785;
6. e) R. F. Heck, Palladium Reagents in Organic Syntheses, Academic Press, London, 1985;
7. f) A. Behr, Aspects of Homogeneous Catalysis, Vol. 5, (Ed.: R. Ugo), D. Reidel Publishing Company, Dordrecht, 1984, p. 3;
8. g) W. Keim, A. Behr, M. Röper, Comprehensive Organometallic Chemistry, Vol. 8 (Eds,: G. Wilkinson, F, 6. A. Stone, E.W. Abel), Pergamon Press, Oxford, 1982, p. 372. For mechanistic investigations, see:
9. h) F. Vollmüller, J. Krause, S. Klein, W. Mägerlein, M. Beller, Eur. J. Inorg. Chem. 2000, 1825-1832;
10. i) A. Behr, G.V. llsemann, W. Keim, C. Krüger, Y.-H. Tsay, Organometallcs 1986, 5, 514-518;
11. j) R. Benn, P.W. Jolly, T. Joswig, R. Mynott, K.-P. Schick, Z. Naturforschung 1986, 41b, 680-691;
12. k) P. W. Jolly, R. Mynott, B. Raspel, K.-P. Schick, Organometallics 1986, 5, 473-481;
13. l) P. W. Jolly, Angew. Chem. 1985, 97, 279-291;
14. Angew. Chem. Int. Ed. Engl. 1985, 24, 283-295;
15. m) R. Benn, P.W. Jolly, R. Mynott, B. Raspel, G. Schenker, K.-P. Schick, G. Schroth, Organometallics 1985, 4, 1945-1953;
16. n) A. Döhring, P.W. Jolly, R. Mynott, K.-P. Schick, G. Wilke, Z. Naturforschung 1981, 36b, 1198-1199.
17. a) R. C. Nunes, M. H. Araujo, E. N. Santos, Catal. Commun. 2007, 8, 1798-1802;
18. b) B. Blanco, M. Brissart, M. Moreno-Manas, R. Pleixats, A. Mehdi, C. Reye, S. Bouquillon, F. Henin, J. Muzart, Appl. Catal. A: Gen. 2006, 297, 117-124;
19. c) L Magna, Y. Chauvin, G. P. Niccolai, Organometallics 2003, 22, 4418-4425;
20. d) B. Estrine, B. Blanco, S. Bouquillon, Tetrahedron Lett. 2001, 42, 7055-7057;
21. e) F. Vollmüller, W. Mägerlein, S. Klein, J. Krause, M. Beller, Adv. Synth. Catal. 2001, 343, 29-33;
22. f) M. Basato, L. Crociani, F. Benvenuti, A.M. Raspolli Galletti, G. Sbrana, J. Mol. Catal. A: Chem. 1999, 145, 313-316;
23. g) F. Benvenuti, C. Carlini, M. Lami, M. Marchionna, R. Patrini, A. M. Raspolli Galletti, G. Sbrana, J. Mol. Catal. A: Chem. 1999, 144, 27-40;
24. h) F. Benvenuti, C. Carlini, M. Marchionna, R. Patrini, A. M. Raspolli Galletti, G. Sbrana, J. Mol. Catal. A: Chem. 1999, 140, 139-155;
25. i) R. Patrini, M. Lami, M. Marchionna, J. Mol. Catal. A: Chem. 1998, 129, 179-189;
26. j) M. Camargo, P. Dani, J. Dupont, R. F. de Souza, M. Pfeffer, I. Tkatchenko, J. Mol. Catal. A: Chem. 1996, 109, 127-131;
27. k) M. Perree-Fauvet, Y. Chauvin, Tetrahedron Lett. 1975, 16, 4559-4562;
28. I) E.J. Smutny, J. Am. Chem. Soc. 1967, 89, 6793-6794;
29. m) S. Takahashi, T. Shibano, N. Hagihara, Tetrahedron Lett. 1967, 26, 2451-2453.
30. a) G. V. Shanbhag, S. M. Kumbar, T. Joseph, S. B. Halligudi, Tetrahedron Lett. 2006, 47, 141-143;
31. b) F. Leca, R. Reau, J. Catal. 2006, 238, 425-429;
32. c) M. S. Viciu, F. K. Zinn, E. D. Stevens, S. P. Nolan, Organometallics 2003, 22, 3175;
33. d) G. Santos Fonseca, R. F. De Souza, J. Dupont, Catal. Commun. 2002, 3, 377-380;
34. e) T. Prinz, B. Driessen-Holscher, Chem. Eur. J. 1999, 5, 2069-2076;
35. f) M. L. Chemyshev, V. S. Tkach, T.V. Dmitrieva, G. V. Ratovskii, S. V. Zinchenko, F. K. Shmidt, React. Kinet. Catal. Lett. 1997, 38, 527-531;
36. g) T. Prinz, W. Keim, B. Driessen Holscher, Angew. Chem. 1996, 108, 1835-1836;
37. Angew. Chem. Int. Ed. Engl. 1996, 35, 1708-1710;
38. h) W. Keim, K.-R. Kurtz, M. Röper, J. Mol. Catal. 1983, 20, 129-138;
39. i) W. Keim, M. Röper, J. Org. Chem. 1981, 46, 3702-3707;
40. j) J. Beger, F. Meier, J. Prakt. Chem. 1980, 322, 69-80;
41. k) U. M. Dzhemilev, R. N. Fakhretdinov, A. G. Telin, M. Yu. Dolomatov, E. G. Galkin, G. A. Tolstikov, Russ. Chem. Bull. 1980, 89, 29, 148-152;
42. l) M. Green, G. Scholes, F. G. A. Stone, J. Chem. Soc., Dalton Trans. 1978, 309-314;
43. m) E. Smutny, J. Ann. N. Y. Acad. Sci. 1973, 214, 125-142.
44. a) B. I. Lee, K. H. Lee, J. S. Lee, J. Mol. Catal. A: Chem. 2001, 166, 233-242;
45. b) J. E. L. Dullius, P. A. Z. Suarez, S. Einloft, R. F. De Souza, J. Dupont, J. Fischer, A. DeCian, Organometallics 1998, 17, 815-819;
46. c) E. Monflier, P. Bourdauducq, J.-L Couturier, WO 9526948, 1995;
47. d) E. Monflier, P. Bourdauducq, J.-L. Couturier, J. Kervennal, A. Mortreux, J. Mol. Catal. A: Chem. 1995, 97, 29-33;
48. e) E. Monflier, P. Bourdauducq, J.-L. Couturier, J. Kervennal, I. Suisse, A. Mortreux, Catal. Lett. 1995, 34, 201-212;
49. f) E. Monflier, P. Bourdauducq, J.-L. Couturier, J. Kervennal, A. Mortreux, Appl. Catal. 1995, 131, 167-178;
50. g) U.M. Dzhemilev, V. V. Sidorova, R.V. Kunakova, Izv. Akad. Nauk SSSR Ser. Khim. 1983, 3, 584-588.
51. a) A. Behr, P. Bahke, B. Klinger, M. Becker, J. Mol. Catal. A: Chem. 2007, 267, 149-156;
52. b) A. Behr, M. Heite, Chem. Eng. Technol. 2000, 23, 952-955;
53. c) A. Behr, M. Heite, Chem. Ing. Tech. 2000, 72, 58-61;
54. d) E. Dinjus, W. Leitner, Appl. Organomet. Chem. 1995, 9, 43-50;
55. e) P. Braunstein, D. Matt, D. Nobel, J. Am. Chem. Soc. 1988, 110, 3207-3212;
56. f) A. Musco, C. Perego, V. Tartiari, Inorg. Chim. Acta 1978, 28, L147-L148.
57. a) A. Rodriguez, M. Normen, B. W. Spur, J.-J. Godfroid, T. H. Lee, Eur. J. Org. Chem. 2000, 2991-3000;
58. b) J. Tsuji, Y. Kobayashi, T. Takahasi, Tetrahedron Lett. 1980, 21, 483-486;
59. c) J. Tsuji, I. Shimizu, H. Suzuki, Y. Naito, J. Am. Chem. Soc 1979, 101, 5070-5072;
60. d) J. Tsuji, H. Yasuda, T. Mandai, J. Org. Chem. 1978, 43, 3606-3607;
61. e) J. Tsuji, T. Mandai, Tetrahedron Lett. 1978, 19, 1817-1820;
62. f) J. Tsuji, K. Mizutani, I. Shimizu, K. Yamamoto, Chem. Lett. 1976, 773-774.
63. a) E. Monflier, P. Bourdauducq, J.-L. Couturier, J. Kervennal, A. Mortreux, Appl. Catal. 1995, 131, 167-178;
64. b) E. Monflier, P. Bourdauducq, J.-L. Couturier, J. Kervennal, I, Suisse, A. Mortreux, Catal. Lett. 1995, 34, 201-212;
65. c) N. Yoshimura, M. Tamura, (Kuraray) US 4,356,333, 1981; [Chem. Abstr. 1982, 103630].
66. a) F. Benvenuti, C. Carlini, A. M. Raspolli Galletti, G. Sbrana, M. Marchionna, R. Patrini, J. Mol. Catal. A: Chem. 1999, 137, 49-63;
67. b) M. Marchionna, R. Patrini, F. Giazzi, G. C. Pecci, 212th National Meeting of the American Chemical Society, Div. Petrol. Chem. 1996, 41, 585.
68. a) W von Rybinski, K. Hill, Angew. Chem. 1998, 110, 1394-1412;
69. Angew. Chem. Int. Ed. 1998, 37, 1328-1345;
70. b) B. Gruber, K.J. Weese, S. M. Hoagland, H. P. Mueller, K. Hill, A. Behr, (Henkel) DE 4242467, 1992;
71. c) B. Gruber, K. J. Weese, S.M. Hoagland, H. P. Mueller, K. Hill, A. Behr, (Henkel) WO 1990, 13531, 1990;
72. [Chem. Abstr. 1991, 115, 137003].
73. J. Falbe, H. Bahrmann, W. Lipps, D. Mayer, Ullmann's Encyclopedia of Industrial Chemistry, Vol. A1 (Eds.: W. Gerhartz, Y. S. Yamamoto, F. T. Campbell, R. Pfefferkorn, J. F. Rounsaville), VCH, Weinheim, 1985, p. 279.
74. a) Aqueous-Phase Organometallic Catalysis, 2nd ed. (Eds.: B. Cornils, W. A. Herrmann), Wiley-VCH, Weinheim, 2004;
75. b) Y. Tokitoh, T. Higashi, K. Hino, M. Murasawa, N. Yoshimura, (Kuraray) EP 436226, 1991 [Chem. Abstr. 1991, 115, 158508];
76. c) Y. Tokitoh, T. Higashi, K. Hino, M. Murasawa, N. Yoshimura, (Kuraray) US 5118885, 1992;
77. d) G. B. Jacobsen, H. L. Pelt, B. J. Schaart, (Dow Benelux) WO 91/09822, 1989;
78. e) R. C. Bohley, G. B. Jacobsen, H. L Pelt, B. J. Schaart, D. A. G. Van Oeffelen, (Dow Benelux) WO 92/10450, 1992;
79. f) B. J. Schaart, H. L. Pelt, G. B. Jacobsen, (Dow) US 5254782, 1993.
80. 1,3-Butadiene: a) A. Grotevendt, M. Bartolome, D. J. Nielsen, A. Spannenberg, R. Jackstell, K. J. Cavell, L. A. Oro, M. Beller, Tetrahedron Lett. 2007, 48, 9203-9207;
81. b) S. Harkal, R. Jackstell, F. Nierlich, D. Ortmann, M. Beller, Org. Lett. 2005, 7, 541-544;
82. c) R. Jackstell, S. Harkal, H. Jiao, A. Spannenberg, C. Borgmann, D. Rottger, F. Nierlich, M. Elliot, S. Niven, K. Cavell, O. Navarro, M. S. Viciu, S. P. Nolan, M. Beller, Chem. Eur. J. 2004, 10, 3891-3900;
83. d) R. Jackstell, M.G. Andreu, A. Frisch, K. Selvakumar, A. Zapf, H. Klein, A. Spannenberg, D. Röttger, O. Briel, R. Karch, M. Beller, Angew. Chem. 2002, 114, 1028-1031;
84. Angew. Chem. Int. Ed. 2002, 41, 986-989;
85. e) R. Jackstell, A. Frisch, M. Beller, D. Röttger, M. Malaun, B. Bildstein, J. Mol. Catal. A: Chem. 2002, 185, 105-112. Isoprene:
86. f) R. Jackstell, A. Grotevendt, D. Michalik, L. E. Firdoussi, M. Beller, J. Organomet. Chem. 2007, 692, 4737-4744.
87. a) R. Palkovits, I. Nieddu, R.J. M. Klein Gebbink, B. M. Weckhuysen, Chem. Sus. Chem 2008, 7, 193-196;
88. b) B. Gruber, B. Fabry, B. Giesen, R. Mueller, F. Wangemann, Tenside Surfactants Deterg. 1993, 30, 422-426.
89. a) B. Estrine, S. Bouquillon, F. Henin, J. Muzart, Appl. Organomet. Chem. 2007, 21, 945-946;
90. b) C. Hadad, C. Damez, S. Bouquillon, B. Estrine, F. Henin, J. Muzart, I. Pezron, L. Komunjer, Carbohydr. Res. 2006, 341, 1938-1944;
91. c) C. Damez, B. Estrine, A. Bessmertnykh, S. Bouquillon, F. Henin, J. Muzart, J. Mol. Catal. A: Chem. 2006, 244, 93-98;
92. d) A. Bessmertnykh, F. Henin, A. Serra-Muns, J. Muzart, H. Baillia, Carbohydr. Res. 2006, 341, 153-159;
93. e) C. Hadad, C. Damez, S. Bouquillon, B. Estrine, F. Henin, J. Muzart, I. Pezron, L. Komunjer, Carbohydr. Res. 2006, 341, 1938-1944;
94. f) A. Bessmertnykh, F. Henin, J. Muzart, J. Mol. Catal. A: Chem. 2005, 238, 199-206;
95. g) B. Estrine, S. Bouquillon, F. Henin, J. Muzart, Green Chem. 2005, 7, 219-223;
96. h) F. Hénin, A. Bessmertnykh, A. Serra-Muns, J. Muzart, H. Baillia, Eur. J. Org. Chem. 2004, 511-520;
97. i) B. Estrine, S. Bouquillon, F. Hénin, J. Muzart, Eur. J. Org. Chem. 2004, 2914-2922;
98. j) C. Donzé, C. Pinel, P. Gallezot, P. L. Taylor, Adv. Synth. Catal. 2002, 344, 906-910;
99. k) V. Desvergnes-Breuil, C. Pinel, P. Gallezot, Green Chem. 2001, 3, 175-177;
100. l) I. Pennequin, J. Meyer, I. Suisse, A. Mortreux, J. Mol. Catal. A: Chem. 1997, 120, 139-142;
101. m) K. Hill, K. J. Gruber, K.J. Weese, Tetrahedron Lett. 1994, 35, 4541-4542.
102. a) A. B. Sorokin, S. L. Kachkarova-Sorokina, C. Donzé, C. Pinel, P. Gallezot, Top. Catal. 2004, 27, 67-76;
103. b) U. Donze, C. Pinel, P. Gallezot, P. L. Taylor, Adv. Synth. Catal. 2002, 344, 906-910.
104. a) U.M. Dzhemilev, R. V. Kunakova, N. Z. Baibulatova, G. A. Tolstikov, LM. Zelenova, Russ. Chem. Bull. 1980, 34, 1506-1510;
105. Izv. Akad. Nauk SSSR, Ser. Khim. 1981, 8, 1837-1842;
106. b) U. M. Dzhemilev, R.V. Kunakova, N. Z. Baibulatova, G. A. Tolstikov, A. A. Panasenko, Zh. Org. Khim. 1980, 16, 1157-1161.
107. a) A. Behr, R. Roll, Chem. Ing. Tech. 2005, 77, 748-752;
108. b) A. Behr, M. Urschey, Adv. Synth. Catal. 2003, 345, 1242-1246;
109. c) A. Behr, M. Urschey, V. A. Brehme, Green Chem. 2003, 5, 198-204;
110. d) A. Behr, M. Urschey, J. Mol. Catal. A: Chem. 2003, 197, 101-113.
111. a) J. Muzart, F. Henin, B. Estrine, S. Bouquillon, (CNRS, France; Universite de Reims Champagne Ardenne) FR 2833593 A1, 2003;
112. b) M. Okutsu, T. Kitsuki, A. Nagasawa, (Kao Corp., Japan) EP 1160232 A2, 2001;
113. c) M. Okutsu, A. Nagasawa, T. Kitsuki, (Kao Corp., Japan) JP 2001039914 A, 2001
114. d) I. Pennequin, A. Mortreux, F. Petit, J. Mentech, B. Thiriet (Eridania Beghin Say) FR 19940107, 1994 [Chem. Abstr. 1994, 121, 205887];
115. e) R. Patrini, M. Marchionna, (Snamprogetti SpA, Italy) EP 613875 A1, 1994;
116. f) J. Meixner, J. Pedain, K. H. Buechel, H. J. Traenckner, (Bayer AG) EP 522400 A2, 1993;
117. g) K, Hill, S. D. Axt, K. J. Weese, WO 9302032; [Chem. Abstr. 1993, 35, 4541-4542];
118. h) B. Gruber, U, Eicken, N. Stork, (Henkel KGaA) DE 4129528 A1, 1993;
119. i) T. Markert, B. Gruber, K. Bruns, (Henkel KGaA) DE 4021015 A1, 1992;
120. j) B. Fabry, B. Gruber, (Henkel KGaA) DE 4020973 A1, 1992;
121. k) H. C. Raths, B. Gruber, D. Ouzounis, (Henkel KGaA) DE 4021478 A1, 1992;
122. l) R. Bunte, B, Gruber, J. Tucker, (Henkel KGaA) DE 4021511 A1, 1992.