Arene-ruthenium(II) complexes containing inexpensive tris(dimethylamino) phosphine: Highly efficient catalysts for the selective hydration of nitriles into amides

Organometallics

Volumn 30, Issue 20, 2011, Pages 5442-5451

  García Álvarez, Rocío ^a   Díez, Josefina ^a   Crochet, Pascale ^a   Cadierno, Victorio ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYTIC HYDRATION; EFFICIENT CATALYSTS; NEUTRAL CONDITIONS; ORGANONITRILES; X RAY CRYSTAL STRUCTURES;

AMIDES; CRYSTAL STRUCTURE; CYANIDES; FUNCTIONAL GROUPS; HYDRATION; LIGANDS; PHOSPHORUS COMPOUNDS; RUTHENIUM; TOLUENE;

RUTHENIUM COMPOUNDS;

EID: 80054748823     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om2006563     Document Type: Article

References (142)

1. Zabicky, J., Ed. The Chemistry of Amides; Wiley: New York, 1970.
2. Greenberg, A., Breneman, C. M., and Liebman, J. F., Eds. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Materials Science; Wiley: New York, 2000.
3. Deopura, B. L., Gupta, B., Joshi, M., and Alagirusami, R., Eds. Polyesters and Polyamides; CRC Press: Boca Raton, FL, 2008.
4. Johansson, I. Kirk-Othmer Encyclopedia of Chemical Technology; Wiley: New York, 2004; Vol. 2, pp 442-463.
5. For a recent general review on metal-catalyzed approaches to amide bond formation, see: Allen, C. L.; Williams, J. M. J. Chem. Soc. Rev. 2011, 40, 3405
6. Bailey, P. D.; Mills, T. J.; Pettecrew, R.; Price, R. A. In Comprehensive Organic Functional Group Transformations II; Katritzky, A. R.; Taylor, R. J. K., Eds.; Elsevier: Oxford, U.K., 2005; Vol. 5, pp 201-294.
7. Dopp, D.; Dopp, H., Eds. Methoden der Organischen Chemie (Houben Weyl); Thieme Verlag: Stuttgart, Germany, 1985; Vol. E5(2), pp 1024-1031.
8. Kobayashi, M.; Shimizu, S. Curr. Opin. Chem. Biol. 2000, 4, 95
9. Endo, I.; Nojori, M.; Tsujimura, M.; Nakasako, M.; Nagashima, S.; Yohda, M.; Odaka, M. J. Inorg. Biochem. 2001, 83, 247
10. Mylerová, V.; Martínková, L. Curr. Org. Chem. 2003, 7, 1279
11. Kovacs, J. A. Chem. Rev. 2004, 104, 825
12. De Santis, G.; Di Cosimo, R. In Biocatalysis for the Pharmaceutical Industry: Discovery, Development and Manufacturing; Tao, J.; Lin, G.-Q.; Liese, A., Eds.; Wiley-VCH: Weinheim, Germany, 2009; pp 153-181.
13. Prasad, S.; Bhalla, T. C. Biotechnol. Adv. 2010, 28, 725
14. Yamaguchi, K.; Matsushita, M.; Mizuno, N. Angew. Chem., Int. Ed. 2004, 43, 1576
15. Bazi, F.; El Badaoui, H.; Tamani, S.; Sokori, S.; Solhy, A.; Macquarrie, D. J.; Sebti, S. Appl. Catal., A 2006, 301, 211
16. Polshettiwar, V.; Varma, R. S. Chem.-Eur. J. 2009, 15, 1582
17. Mitsudome, T.; Mikami, Y.; Mori, H.; Arita, S.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Chem. Commun. 2009, 3258
18. Ishizuka, A.; Nakazaki, Y.; Oshiki, T. Chem. Lett. 2009, 38, 360
19. Yamaguchi, K.; Mizuno, N. Synlett 2010, 2365
20. Kim, A. Y.; Bae, H. S.; Park, S.; Park, S.; Park, K. H. Catal. Lett. 2011, 141, 685
21. García-Garrido, S. E.; Francos, J.; Cadierno, V.; Basset, J.-M.; Polshettiwar, V. ChemSusChem 2011, 4, 104
22. Parkins, A. W. Platinum Met. Rev. 1996, 40, 169
23. Kukushkin, V. Y.; Pombeiro, A. J. L. Chem. Rev. 2002, 102, 1771
24. Kukushkin, V. Y.; Pombeiro, A. J. L. Inorg. Chim. Acta 2005, 358, 1
25. Ahmed, T. J.; Knapp, S. M. M.; Tyler, D. R. Coord. Chem. Rev. 2011, 255, 949
26. Yamada, H.; Kobayashi, M. Biosci., Biotechnol., Biochem. 1996, 60, 1391
27. van Pelt, S.; van Rantwijk, F.; Sheldon, R. A. Focus on Catalysis Applications (supplement to Chimica Oggi/Chemistry Today); Teknoscienze Srl: Milano, Italy, 2008; Vol. 26, pp 2-4.
28. Sanchez, S.; Demain, A. L. Org. Process Res. Dev. 2011, 15, 224
29. Li, B.; Su, J.; Tao, J. Org. Process Res. Dev. 2011, 15, 291
30. Murahashi, S.-I.; Sasao, S.; Saito, E.; Naota, T. J. Org. Chem. 1992, 57, 2521
31. Murahashi, S.-I.; Sasao, S.; Saito, E.; Naota, T. Tetrahedron 1993, 49, 8805
32. Murahashi, S.-I.; Takaya, H. Acc. Chem. Res. 2000, 33, 225
33. Ghaffar, T.; Parkins, A. W. Tetrahedron Lett. 1995, 36, 8657
34. Akisanya, J.; Parkins, A. W.; Steed, J. W. Org. Process Res. Dev. 1998, 2, 274
35. Ghaffar, T.; Parkins, A. W. J. Mol. Catal. A: Chem. 2000, 160, 249
36. Jiang, X.-B.; Minnaard, A. J.; Feringa, B. L.; de Vries, J. G. J. Org. Chem. 2004, 69, 2327
37. Oshiki, T.; Yamashita, H.; Sawada, K.; Utsunomiya, M.; Takahashi, K.; Takai, K. Organometallics 2005, 24, 6287
38. Goto, A.; Endo, K.; Saito, S. Angew. Chem., Int. Ed. 2008, 47, 3607
39. Cadierno, V.; Francos, J.; Gimeno, J. Chem.-Eur. J. 2008, 14, 6601
40. Cadierno, V.; Díez, J.; Francos, J.; Gimeno, J. Chem.-Eur. J. 2010, 16, 9808
41. García-Álvarez, R.; Díez, J.; Crochet, P.; Cadierno, V. Organometallics 2010, 29, 3955
42. Chin, C. S.; Kim, S. Y.; Joo, K.-S.; Won, G.; Chong, D. Bull. Korean Chem. Soc. 1999, 20, 535
43. Djoman, M. C. K.-B.; Ajjou, A. N. Tetrahedron Lett. 2000, 41, 4845
44. Kopylovich, M. N.; Kukushkin, V. Y.; Haukka, M.; Fraústo da Silva, J. J. R.; Pombeiro, A. J. L. Inorg. Chem. 2002, 41, 4798
45. Breno, K. L.; Pluth, M. D.; Tyler, D. R. Organometallics 2003, 22, 1203
46. Fung, W. K.; Huang, X.; Man, M. L.; Ng, S. M.; Hung, M. Y.; Lin, Z.; Lau, C. P. J. Am. Chem. Soc. 2003, 125, 11539
47. Breno, K. L.; Pluth, M. D.; Landorf, C. W.; Tyler, D. R. Organometallics 2004, 23, 1738
48. Crestani, M. G.; Arévalo, A.; García, J. J. Adv. Synth. Catal. 2006, 348, 732
49. Crisóstomo, C.; Crestani, M. G.; García, J. J. J. Mol. Catal. A: Chem. 2007, 266, 139
50. Ahmed, T. J.; Zakharov, L. N.; Tyler, D. R. Organometallics 2007, 26, 5179
51. Ashraf, S. M.; Berger, I.; Nazarov, A. A.; Hartinger, C. G.; Koroteev, M. P.; Nifantév, E. E.; Keppler, B. K. Chem. Biodiversity 2008, 5, 1640
52. Ashraf, S. M.; Kandioller, W.; Mendoza-Ferri, M.-G.; Nazarov, A. A.; Hartinger, C. G.; Keppler, B. K. Chem. Biodiversity 2008, 5, 2060
53. Crestani, M. G.; Steffen, A.; Kenwright, A. M.; Batsanov, A. S.; Howard, J. A. K.; Marder, T. B. Organometallics 2009, 28, 2904
54. Crestani, M. G.; García, J. J. J. Mol. Catal. A: Chem. 2009, 299, 26
55. Crisóstomo, C.; Crestani, M. G.; García, J. J. Inorg. Chim. Acta 2010, 363, 1092
56. Cavarzan, A.; Scarso, A.; Struckul, G. Green Chem. 2010, 12, 790
57. Anastas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: Oxford, U.K., 1998.
58. Anastas, P. T.; Williamson, T. C. Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes; Oxford University Press: New York, 1998.
59. Matlack, A. S. Introduction to Green Chemistry; Marcel Dekker: New York, 2001.
60. Lancaster, M. In Handbook of Green Chemistry and Technology; Clark, J. H.; Macquarrie, D. J., Eds.; Blackwell Publishing: Abingdon, U.K., 2002.
61. Lancaster, M. Green Chemistry: An Introductory Text; RSC: London, 2002.
62. Poliakoff, M.; Fitzpatrick, J. M.; Farren, T. R.; Anastas, P. T. Science 2002, 297, 807
63. Anastas, P. T.; Kirchhoff, M. M. Acc. Chem. Res. 2002, 35, 686
64. Sheldon, R. A.; Arends, I.; Hanefeld, U. Green Chemistry and Catalysis; Wiley-VCH: Weinheim, Germany, 2007.
65. Li, C.-J. Chem. Rev. 1993, 93, 2023
66. Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741
67. Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; John Wiley & Sons: New York, 1997.
68. Lindström, U. M. Chem. Rev. 2002, 102, 2751
69. Li, C.-J. Chem. Rev. 2005, 105, 3095
70. Andrade, C. K. Z.; Alves, L. M. Curr. Org. Chem. 2005, 9, 195
71. Li, C.-J.; Chen, L. Chem. Soc. Rev. 2006, 35, 68
72. Herrerías, C. I.; Yao, X.; Li, Z.; Li, C. J. Chem. Rev. 2007, 107, 2546
73. Lindström, U. M., Ed. Organic Reactions in Water; Blackwell Publishing: Oxford, U.K., 2007.
74. Li, C.-J.; Chan, T. H. Comprehensive Organic Reactions in Aqueous Media; Wiley-VCH: Weinheim, Germany, 2007.
75. Skouta, R. Green Chem. Lett. Rev. 2009, 2, 121
76. Anastas, P. T.; Li, C.-J., Eds. Handbook of Green Chemistry; Wiley-VCH: Weinheim, Germany, 2010; Vol. 5.
77. Nelson, W. M. Green Solvents for Chemistry: Perspectives and Practice; Oxford University Press: New York, 2003.
78. Clark, J. H.; Taverner, S. J. Org. Process Res. Dev. 2007, 11, 149
79. Kerton, F. M. Alternative Solvents for Green Chemistry; RSC Publishing: Cambridge, U.K., 2009.
80. 3}] to the catalytic synthesis of the nonsteroidal anti-inflammatory drug ibuprofenamide by hydration of 2-(4-isobutylphenyl)propionitrile has been communicated in a preliminary report: García-Álvarez, R.; Francos, J.; Crochet, P.; Cadierno, V. Tetrahedron Lett. 2011, 52, 4218
81. Bennett, M. A.; Smith, A. K. J. Chem. Soc., Dalton Trans. 1974, 233
82. Bennett, M. A.; Huang, T.-N.; Matheson, T. W.; Smith, A. K. Inorg. Synth. 1982, 21, 74
83. Hull, J. W.; Gladfelter, W. L. Organometallics 1984, 3, 605
84. 1H NMR resonances: Werner, H.; Werner, R. Chem. Ber. 1982, 115, 3766
85. 3 (33 equiv) in dichloromethane for 24 h, has also been previously described: Boshaala, A. M. A.; Simpson, S. J.; Autschbach, J.; Zheng, S. Inorg. Chem. 2008, 47, 9279
86. Le Bozec, H.; Touchard, D.; Dixneuf, P. H. Adv. Organomet. Chem. 1989, 29, 163
87. Bennett, M. A. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 7, pp 549-602.
88. Bennett, M. A. Coord. Chem. Rev. 1997, 166, 225
89. Pigge, F. C.; Coniglio, J. J. Curr. Org. Chem. 2001, 5, 757
90. Kündig, E. P. Top. Organomet. Chem. 2004, 7, 3
91. Gimeno, J.; Cadierno, V.; Crochet, P. In Comprehensive Organometallic Chemistry III; Crabtree, R. H.; Mingos, D. M. P., Eds.; Elsevier: Oxford, U.K., 2007; Vol. 6, pp 465-550.
92. Therrien, B. Coord. Chem. Rev. 2009, 253, 493
93. Cadierno, V.; Díez, J.; García-Álvarez, J.; Gimeno, J. Chem. Commun. 2004, 1820
94. Arquier, D.; Vendier, L.; Miqueu, K.; Sotiropoulos, J.-M.; Bastin, S.; Igau, A. Organometallics 2009, 28, 4945 and references cited therein
95. Redwine, K. D.; Hansen, H. D.; Bowley, S.; Isbell, J.; Sanchez, M.; Vodak, D.; Nelson, J. H. Synth. React. Inorg. Met.-Org. Chem. 2000, 30, 379
96. Nelson, J. H.; Ghebreyessus, K. Y. Organometallics 2000, 19, 3387
97. Nelson, J. H.; Ghebreyessus, K. Y. Synth. React. Inorg. Met.-Org. Chem. 2003, 33, 1329
98. Chaplin, A. B.; Dyson, P. J. Organometallics 2007, 26, 2447
99. Wang, L.; Zhuo, X.-G.; Li, R. X. Acta Crystallogr., Sect. E 2008, E64, m429. See also reference 18
100. Aktas, H.; Slootweg, J. C.; Schakel, M.; Ehlers, A. W.; Lutz, M.; Spek, A. L.; Lammertsma, K. J. Am. Chem. Soc. 2009, 131, 6666
101. Mitzel, N. W.; Smart, B. A.; Dreihäupl, K.-H.; Rankin, D. W. H.; Schmidbaur, H. J. Am. Chem. Soc. 1996, 118, 12673
102. Wang, K.; Emge, T. J.; Goldman, A. S. Organometallics 1994, 13, 2135
103. Brunet, J.-J.; Diallo, O.; Donnadieu, B.; Roblou, E. Organometallics 2002, 21, 3388
104. Blagg, R. J.; Adams, C. J.; Charmant, J. P. H.; Connelly, N. G.; Haddow, M. F.; Hamilton, A.; Knight, J.; Orpen, A. G.; Ridgway, B. M. Dalton Trans. 2009, 8724
105. Dallinger, D.; Kappe, O. C. Chem. Rev. 2007, 107, 2563
106. Polshettiwar, V.; Varma, R. S. Chem. Soc. Rev. 2008, 37, 1546
107. Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629
108. Polshettiwar, V.; Varma, R. S., Eds. Aqueous Microwave-Assisted Chemistry; RSC: Cambridge, U.K., 2010.
109. Spickett, R. G. W.; Vega, A.; Prieto, J.; Moragues, J.; Marquez, M.; Roberts, D. J. Eur. J. Med. Chem. 1976, 11, 7
110. Allegretti, M.; Bertini, R.; Cesta, M. C.; Bizzarri, C.; Di Bitondo, R.; Di Cioccio, V.; Galliera, E.; Berdini, V.; Topai, A.; Zampella, G.; Russo, V.; Di Bello, N.; Nano, G.; Nicolini, L.; Locati, M.; Fantucci, P.; Florio, S.; Colotta, F. J. Med. Chem. 2005, 48, 4312
111. Rajasekaran, A.; Sivakumar, P.; Jayakar, B. Indian J. Pharm. Sci. 1999, 61, 158
112. Bertini, R.; Bizzarri, C.; Sabbatini, V.; Porzio, S.; Caselli, G.; Allegretti, M.; Cesta, M. C.; Gandolfi, C. A.; Mantovanini, M.; Colotta, F. PCT International Patent Application WO2000024710, 2000.
113. Nakatsuka, M.; Nakatani, S.; Okada, S.-I.; Tsuboi, K.; Nishikaku, F. PCT International Patent Application WO2001005774, 2001.
114. Doshi, A.; Samant, S. D.; Deshpande, S. G. Indian J. Pharm. Sci. 2002, 64, 440
115. Doshi, A.; Deshpande, S. G. Indian J. Pharm. Sci. 2002, 64, 445
116. Bertini, R.; Allegretti, M.; Bizzarri, C.; Moriconi, A.; Locati, M.; Zampella, G.; Cervellera, M. N.; Di Cioccio, V.; Cesta, M. C.; Galliera, E.; Martinez, F. O.; Di Bitondo, R.; Troiani, G.; Sabbatini, V.; D'Anniballe, G.; Anacardio, R.; Cutrin, J. C.; Cavalieri, B.; Mainiero, F.; Strippoli, R.; Villa, P.; Di Girolamo, M.; Martin, F.; Gentile, M.; Santoni, A.; Corda, D.; Poli, G.; Mantovani, A.; Ghezzi, P.; Colotta, F. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11791
117. Allegretti, M.; Cesta, M. C.; Nano, G.; Bertini, R.; Bizzarri, C.; Colotta, F. PCT International Patent Application WO2005028425, 2005.
118. Guo, C. B.; Cai, Z. F.; Guo, Z. R.; Feng, Z. Q.; Chu, F. M.; Cheng, G. F. Chin. Chem. Lett. 2006, 17, 325
119. Doshi, A.; Deshpande, S. G. Indian J. Pharm. Sci. 2007, 69, 824
120. Marjanović, M.; Zorc, B.; Pejnović, L.; Zovko, M.; Kralj, M. Chem. Biol. Drug Des. 2007, 69, 222
121. Beard, T.; Cohen, M. A.; Parratt, J. S.; Turner, N. J.; Crosby, J.; Moilliet, J. Tetrahedron: Asymmetry 1993, 4, 1085
122. Fallon, R. D.; Stieglitz, B.; Turner, I. Appl. Microbiol. Biotechnol. 1997, 47, 156
123. Effenberger, F.; Graef, B. W. J. Biotechnol. 1998, 60, 165
124. Bauer, R.; Knackmuss, H.-J.; Stolz, A. Appl. Microbiol. Biotechnol. 1998, 49, 89
125. Rzeznicka, K.; Schätzle, S.; Böttcher, D.; Klein, J.; Bornscheuer, U. T. Appl. Microbiol. Biotechnol. 2010, 85, 1417
126. Formation of ibuprofenamide 4ag by phase transfer catalyzed oxidation of nitrile 3ag with basic hydrogen peroxide has been described (up to 70% conversion with 90% selectivity was reached): Yadav, G. D.; Ceasar, J. L. Org. Process Res. Dev. 2008, 12, 740
127. The conventional methods of synthesis of 4ag and 4ah involve the conversion of the carboxylic acids ibuprofen and ketoprofen to the corresponding acid chlorides, by action of harmful thionyl chloride, followed by treatment with aqueous or gaseous ammonia. See refs 33 and 34 and: Allegretti, M.; Bertini, R.; Beccari, A.; Moriconi, A.; Aramini, A.; Bizzarri, C.; Colotta, F. PCT International Patent Application WO2006063999, 2006.
128. Burgada, R. Bull. Soc. Chim. Fr. 1972, 4161
129. Montemayor, R. G.; Parry, R. W. Inorg. Chem. 1973, 12, 2482
130. Kraihanzel, C. S. J. Organomet. Chem. 1974, 73, 137
131. Febvay, J.; Casabianca, F.; Riess, J. G. J. Am. Chem. Soc. 1984, 106, 7985
132. Hulst, R.; de Vries, N. K.; Feringa, B. L. Tetrahedron: Asymmetry 1994, 5, 699
133. Dyer, P. W.; Fawcett, J.; Hanton, M. J.; Kemmitt, R. D. W.; Padda, R.; Singh, N. Dalton Trans. 2003, 104
134. Miklášová, N.; Julínek, O.; Mešková, M.; Setnička, V.; Urbanová, M.; Putala, M. Tetrahedron Lett. 2010, 51, 1966
135. 2)] (7b) has been previously described in the literature: DelĺAmico, D. B.; Calderazzo, F.; Labella, L.; Marchetti, F.; Sbrana, E. J. Organomet. Chem. 2002, 651, 52
136. ProRED; Oxford Diffraction Ltd.: Oxford, UK, 2008.
137. Farrugia, L. J. J. Appl. Crystallogr. 1999, 32, 837
138. Beurskens, P. T.; Admiraal, G.; Beurskens, G.; Bosman, W. P.; García-Granda, S.; Gould, R. O.; Smits, J. M. M.; Smykalla, C. The DIRDIF Program System; Technical Report of the Crystallographic Laboratory; University of Nijmegen: Nijmegen, The Netherlands, 1999.
139. Sheldrick, G. M. SHELXL97: Program for the Refinement of Crystal Structures; University of Göttingen: Göttingen, Germany, 1997.
140. International Tables for X-Ray Crystallography; Kynoch Press: Birminghan, U.K., 1974; Vol. IV (present distributor: Kluwer Academic Publishers: Dordrecht, The Netherlands).
141. Nardelli, M. Comput. Chem. 1983, 7, 95
142. Spek, A. L. PLATON: A Multipurpose Crystallographic Tool; University of Utrecht: Utrecht, The Netherlands, 2007.