Ruthenium-catalyzed dimerization of acrylonitrile in the presence of carboxylic acids

Journal of Molecular Catalysis A: Chemical

Volumn 264, Issue 1-2, 2007, Pages 9-16

  Kashiwagi, Kohich ^a,b   Sugise, Ryoji ^a   Shimakawa, Toshihiro ^a   Matuura, Tunao ^a   Shirai, Masashi ^a  

^a UBE INDUSTRIES LTD   (Japan)

^b HIROSHIMA UNIVERSITY   (Japan)

Author keywords

C C bond formation; C H bond activation; Carboxylic acid; Dimerization of acrylonitrile; Ruthenium catalyst

Indexed keywords

CARBOXYLIC ACIDS; CATALYSIS; CHEMICAL BONDS; DIMERIZATION; RATE CONSTANTS; RUTHENIUM;

ACRYLONITRILE; C-C BOND FORMATION; C-H BOND ACTIVATION; LINEAR DIMERS;

ACRYLIC MONOMERS;

EID: 33847233675     PISSN: 13811169     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcata.2006.08.077     Document Type: Article

References (100)

1. Olivier-Bourbigou H., and Saussine L. In: Cornils B., and Herrmann W.A. (Eds). Applied Homogeneous Catalysis with Organometallic Compounds. 2nd ed. vol. 1 (2002), Wiley-VCH, Weinheim 253
2. Parshall G.W., and Ittel S.D. Homogeneous Catalysis: The Application and Chemistry of Catalysis by Soluble Transition Metal Complexes. 2nd ed. (1995), John Wiley and Sons Inc. p. 78
3. Skupinska J. Chem. Rev. 91 (1991) 613
4. Keim W. Angew. Chem., Int. Ed. 29 (1990) 235
5. McGuinness D.S., Mueller W., Wasserscheid P., Cavell K.J., Skelton B.W., White A.H., and Englert U. Organometallics 21 (2002) 175
6. Alderson T., Jenner E., and Lindsey R.V. J. Am. Chem. Soc. 87 (1965) 5638
7. Brookhart M., White P.S., and DiRenzo G.M. J. Am. Chem. Soc. 118 (1996) 6225
8. Small B.L., and Marcucci A.J. Organometallics 20 (2001) 5738
9. Small B.L. Organometallics 22 (2003) 3178
10. Mitsudo T., Suzuki T., Zhang S.-W., Imai D., Fujita K., Manabe T., Shiotsuki M., Watanabe Y., Wada K., and Kondo T. J. Am. Chem. Soc. 121 (1999) 1839
11. Misono A., Uchida Y., Hidai M., and Kanai H. Chem. Commun. (1967) 357
12. McClure J.D., Owyang R., and Slaugh L.H. J. Organomet. Chem. 12 (1968) 8
13. Billig E., Strow C.B., and Pruett R.L. Chem. Commun. (1968) 1307
14. Misono A., Uchida Y., Hidai M., and Inomata I. Chem. Commun. (1968) 704
15. Misono A., Uchida Y., Hidai M., Shinohara H., and Watanabe Y. Bull. Chem. Soc. Jpn. 41 (1968) 396
16. Misono A., Uchida Y., Hidai M., Inomata I., Watanabe Y., and Takeda M. Kogyo Kagaku Zasshi 72 (1969) 1801
17. Misono A., Uchida Y., Hidai M., Inomata I., Watanabe Y., and Takeda M. Chem. Abstr. 72 (1970) 42713
18. Watanabe Y., and Takeda M. Nippon Kagaku Kaishi (1972) 2023
19. Watanabe Y., and Takeda M. Chem. Abstr. 78 (1973) 57347
20. Strohmeier W., and Kaiser A. J. Organomet. Chem. 114 (1976) 273
21. Tsou D.T., Burrington J.D., Maher E.A., and Grasselli R.K. J. Mol. Catal. 30 (1985) 219
22. Tsou D.T., Burrington J.D., Maher E.A., and Grasselli R.K. J. Mol. Catal. 22 (1983) 29
23. Fukuoka A., Nagano T., Furuta S., Yoshizawa M., Hirano M., and Komiya S. Bull. Chem. Soc. Jpn. 71 (1998) 1409
24. Catalytic dimerization of acrylonitrile using organic phosphinite or phosphonite:
25. Jennings J.R., and Cozens R.J. Appl. Catal. A: Gen. 124 (1995) 297
26. Jennings J.R., Cozens R.J., and Wade K. Appl. Catal. A: Gen. 130 (1995) 175
27. Jennings J.R., and Cozens R.J. Appl. Catal. A: Gen. 135 (1996) 163
28. Rhone-Poulenc. Neth. Appl. 6 603 (1966) 115
29. Rhone-Poulenc. Chem. Abstr. 66 (1967) 85483
30. Shinohara H., Watanabe Y., and Suzuki T. Jpn. Tokkyo Koho 24 (1969) 585 (Mitsubishi Petrochemical Co. Ltd.)
31. Shinohara H., Watanabe Y., and Suzuki T. Chem. Abstr. 72 (1970) 42849
32. W.H. Knoth, US Patent 3,538,133 (1970) (du Pont de Nemours, E.I. and Co.)
33. Knoth W.H. Chem. Abstr. 74 (1971) 6970
34. G.W. Godin, Ger. Offen 2,019,907 (1971) (BP Chemicals Ltd.)
35. Godin G.W. Chem. Abstr. 75 (1971) 19734
36. P.F. Todd, Ger. Patent 2,446,641 (1975) (Imperial Chemical Industries Ltd.)
37. Todd P.F. Chem. Abstr. 83 (1975) 27639
38. R.K. Grasselli, J.D. Burrington, F.A. Pesa, H.F. Hardman, Eur. Pat. Appl. 72,231 (1983) (Standard Oil Co.)
39. Grasselli R.K., Burrington J.D., Pesa F.A., and Hardman H.F. Chem. Abstr. 99 (1983) 139364
40. Murai S., Oodan K., Sugise R., Shirai M., and Shimakawa T. Jpn. Kokai Tokkyo Koho 09 (1994) 531 (Ube Industries Ltd.)
41. Murai S., Oodan K., Sugise R., Shirai M., and Shimakawa T. Chem. Abstr. 120 (1994) 191146
42. Yorisue T., and Kanejima S. Jpn. Kokai Tokkyo Koho 245 (1996) 539 (Asahi Chemical Ind.)
43. Yorisue T., and Kanejima S. Chem. Abstr. 126 (1996) 7712
44. Suzuki Y., and Kiso Y. PCT Int. Appl. 1 (1997) 531 (Mitsui Petrochemical Idusties Ltd.)
45. Suzuki Y., and Kiso Y. Chem. Abstr. 126 (1997) 157193
46. Yasuda H. Jpn. Kokai Tokkyo Koho 03 (1999) 544 (Showa Denko K.K.)
47. Yasuda H. Chem. Abstr. 130 (1999) 168018
48. Trost B.M., Toste F.D., and Pinkerton A.B. Chem. Rev. 101 (2001) 2067
49. Ruthenium catalyst:
50. McKinney R.J., and Colton M.C. Organometallics 5 (1986) 1080
51. Ren C.Y., Cheng W.C., Chan W.C., Yeung C.H., and Lau C.P. J. Mol. Catal. 59 (1990) L1
52. Sustmann R., Hornung H.J., Schupp T., and Patzke B. J. Mol. Catal. 85 (1993) 149
53. Pertici P., Ballantini V., Salvadori P., and Bennett M.A. Organometallics 14 (1995) 2565
54. Rh catalyst:
55. Alderson T., Jenner E.L., and Lindsey R.V. J. Am. Chem. Soc. 87 (1965) 5638
56. Nugent W.A., and Mckinney R.J. J. Mol. Catal. 29 (1985) 65.
57. Kaneko Y., Kanke T., Kiyooka S., and Isobe K. Chem. Lett. (1997) 23
58. Hauptman E., Sabo-Etienne S., White P.S., Brookhart M., Garner J.M., Fagan P.J., and Calabrese J.C. J. Am. Chem. Soc. 116 (1994) 8038
59. Pd catalyst:
60. Barlow M.G., Bryant M.J., Haszeldine R.N., and Mackie A.G. J. Organomet. Chem. 21 (1970) 215
61. Oehme G., and Pracejus H. Tetrahedron Lett. (1979) 343
62. Nugent W.A., and Hobbs F.W. J. Org. Chem. 48 (1983) 5364
63. Grenouillient P., Neibecker D., and Tkatchenko I. Organometallics 3 (1984) 1130
64. Ni catalyst:
65. Wilke G. Angew. Chem., Int. Ed. 27 (1988) 185
66. Ohgomori Y., Ichikawa S., and Sumitani N. Organometallics 13 (1994) 3758
67. Parshall G.W., and Ittel S.D. Applied Homogeneous Catalysis. 2nd ed. (1992), Wiley-Interscience, New York 242
68. Weissermel K., and Arpe H.-J. Industrial Organic Chemistry. 2nd ed. (1993), Verlag Chemie, Weinheim, Germany
69. R.J. McKinney, U.S. Patent 4,504,674 (1985).
70. Thomas J.M., Raja R., Sankar G., and Bell R.G. Acc. Chem. Res. 34 (2001) 191
71. Niu W., Draths K.M., and Frost J.W. Biotechnol. Progr. 18 (2002) 201
72. Kiss G. Chem. Rev. 101 (2001) 3435
73. Kashiwagi K., Sugise R., Shimakawa T., Matsuura T., Shirai M., Kakiuchi F., and Murai S. Organometalics 16 (1997) 2233
74. Kashiwagi K., Sugise R., Shimakawa T., Matsuura T., and Shirai M. Chem. Lett. 35 (2006) 186
75. Evans I.P., Spencer A., and Wilkinson G. J. Chem. Soc. Dalton Trans. (1973) 204
76. Morimoto T. Jpn. Tokkyo Koho 49 28 (1974) 731 (Mitsui Petrochemical Industries, Ltd.)
77. Morimoto T. Chem. Abstr. 82 (1975) 86096
78. Sugise R., and Shirai M. Jpn. Kokai Tokkyo Koho 05 255 (1993) 225 (UBE Industries Ltd.)
79. Sugise R., and Shirai M. Chem. Abstr. 120 (1994) 244131
80. 2-Cyanoethyl o-benzoylbenzoate 4b 0.57 g (2.0 mmol) was added initially to the solution used in experimental section 2.4. The conversion of AN was 15.5%. The products and the yields were as follows: cis-1 5.80%, trans-1 6.46%, ADN 2 0.21%, cis,cis-3 0.15%, cis,trans-3 0.52%, trans,trans-3 0.26%, PN 5 0.50% (selectivity 3.2%), and 2-cyanoethyl o-benzoylbenzoate 4b 0.50% (selectivity 3.2%). The overall yield of linear dimers 1-3 was 13.4% (TON 992) and the selectivity for linear dimers 1-3 was 86.5%.
81. Zalewski R.I. In: Patai S. (Ed). The Chemistry of Functional Groups, Supplement B, The Chemistry of Acid Derivatives, Part 1 vol. 2 (1992), John Wiley and Sons 318
82. Braude E.A., and Nachod F.C. Determination of Organic Structures by Physical Methods (1955), Academic Press, New York p. 567
83. Bray G.B., Doppy J.E., and Hughers S.R.C. J. Chem. Soc. (1957) 265
84. Davies H. J. Phys. Chem. 61 (1957) 123
85. The dimer of AN was not given at all when p-toluenesulfonic acid and trifluoroacetic acid were used as the acid. Phenol gave the same results as those in the absence of hydrogen and carboxylic acids.
86. Malik K.Z., Robinson S.D., and Steed J.W. Polyhedron 19 (2000) 1589
87. Milner D.J., and Whelan R.J. J. Organomet. Chem. 152 (1978) 193
88. Masada reported that cis-1 was the major product in the gas-phase dimerization of acrylonitrile
89. Masada T., and Yasui T. Kogyo Kagaku Zasshi 74 (1971) 2405
90. Masada T., and Yasui T. Chem. Abstr. 76 (1972) 33911
91. A similar catalytic cycle involving C-H bond cleavage and a catalytic cycle not involving C-H bond cleavage but involving initial hydrometalation were postulated [5].
92. Similar cis cleavage has been postulated in the work of Ref. [22]. See also a similar stoichiometric reaction of an α,β-unsaturated ester:
93. Komiya S., and Yamamoto A. Chem. Lett. (1975) 475
94. Komiya S., Ito T., Cowie M., Yamamoto A., and Ibers J. J. Am. Chem. Soc. 98 (1976) 3874 (In contrast, trans cleavage has also been suggested; see [5c])
95. Murai and co-workers proposed that the nitrile group of aromatic nitrile was capable of directing ruthenium to the ortho C-H bond via the π-bonded mode:
96. Kakiuchi F., Sonoda M., Tsujimoto T., Chatani N., and Murai S. Chem. Lett. (1999) 1083
97. Trost B.M., Indolese A.F., Muller T.J.J., and Treptow B. J. Am. Chem. Soc. 117 (1995) 615
98. Trost B.M., Toste F.D., and Pinkerton A.B. Chem. Rev. 101 (2001) 2067
99. Fujiwara M., Nishikawa T., and Hori Y. Org. Lett. 1 (1999) 1636
100. Kakiuchi F., and Murai S. Acc. Chem. Res. 35 (2002) 826