Ruthenium N-heterocyclic carbene catalysts for selective reduction of nitriles to primary amines

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3654-3656

  Addis, Daniele ^a   Enthaler, Stephan ^a   Junge, Kathrin ^a   Wendt, Bianca ^a   Beller, Matthias ^a  

^a LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

Homogeneous catalysis; Hydrogenation; Nitriles; Primary amines; Ruthenium

Indexed keywords

1,3 BIS(2,4,6 TRIMETHYLPHENYL) 4,5 DIHYDROIMIDAZOLIUM TETRAFLUOROBORATE; AMINE; BENZONITRILE; BORIC ACID; CARBENE; LIGAND; NITRILE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ENVIRONMENT; HYDROGENATION;

EID: 65549161083     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.108     Document Type: Article

References (84)

1. Lawrence S.A. Amines: Synthesis, Properties, and Application (2004), Cambridge University, Cambridge
2. Hartwig J.F. In: Negishi E.-I. (Ed). Handbook of Organopalladium Chemistry for Organic Synthesis Vol. 1 (2002), Wiley Interscience, New York 1051
3. Selective reviews:. Hartwig J.F. Synlett (2006) 1283-1294
4. Buchwald S.L., Mauger C., Mignani G., and Scholz U. Adv. Synth. Catal. 348 (2006) 23-39
5. Navarro O., Marion N., Mei J., and Nolan S.P. Chem. Eur. J. 12 (2006) 5142-5148
6. Hydroamination reviews:. Hultzsch K.C., Gribkov D.V., and Hampel F. J. Organomet. Chem. 690 (2005) 4441-4452
7. Hartwig J.F. Pure Appl. Chem. 76 (2004) 507-516
8. Doye S. Synlett (2004) 1653-1672
9. Seayad J., Tillack A., Hartung C.G., and Beller M. Adv. Synth. Catal. 344 (2002) 795-813
10. Beller M., Breindl C., Eichberger M., Hartung C.G., Seayad J., Thiel O., Tillack A., and Trauthwein H. Synlett (2002) 1579-1594
11. Hydroaminomethylation:. Buch C., Jackstell R., Bühring M., and Beller M. Chem.-Ing. Technik 79 (2007) 434-441
12. Ahmed M., Buch C., Routaboul L., Jackstell R., Klein H., Spannenberg A., and Beller M. Chem. Eur. J. 13 (2007) 1594-1601
13. Bronger R.P.J., Kamer P.C.J., van Leeuwen P.W.M.N., Ahmed M., Seayad A.M., Jackstell R., and Beller M. Chem. Eur. J. 12 (2006) 8979-8988
14. Müller K.-S., Koç F., Ricken S., and Eilbracht P. Org. Biomol. Chem. 4 (2006) 826-835
15. Routaboul L., Buch C., Klein H., Jackstell R., and Beller M. Tetrahedron Lett. 46 (2005) 7401-7405
16. Moballigh A., Seayad A., Jackstell R., and Beller M. J. Am. Chem. Soc. 125 (2003) 10311-10318
17. Eilbracht P., Bärfacker L., Buss C., Hollmann C., Kitsos-Rzychon B.E., Kranemann C.L., Rische T., Roggenbuck R., and Schmidt A. Chem. Rev. 99 (1999) 3329-3366
18. Reductive amination:. Storer R.I., Carrera D.E., Ni Y., and MacMillan D.W.C. J. Am. Chem. Soc. 128 (2006) 84-86
19. Tararov V.I., and Börner A. Synlett (2005) 203-211
20. For reviews see:. Sundermeier M., Zapf A., and Beller M. Eur. J. Inorg. Chem. (2003) 3513-3526
21. Schareina T., Zapf A., Cotté A., Müller N., and Beller M. Synthesis (2008) 3351-3355
22. Selected examples:. Sundermeier M., Zapf A., Beller M., and Sans J. Tetrahedron Lett. 42 (2001) 6707-6710
23. Sundermeier M., Zapf A., and Beller M. Angew. Chem., Int. Ed. 42 (2003) 1661-1664
24. Sundermeier M., Mutyala S., Zapf A., Spannenberg A., and Beller M. J. Organomet. Chem. 684 (2003) 50-55
25. Sundermeier M., Zapf A., Sateesh M., and Beller M. Chem. Eur. J. 9 (2003) 1828-1836
26. Schareina T., Zapf A., and Beller M. Chem. Commun. (2004) 1388-1389
27. Schareina T., Zapf A., and Beller M. J. Organomet. Chem. 689 (2004) 4576-4583
28. Schareina T., Zapf A., Mägerlein W., Müller N., and Beller M. Chem. Eur. J. 13 (2007) 6249-6254
29. Schareina T., Zapf A., Mägerlein W., Müller N., and Beller M. Synlett (2007) 555-558
30. Schareina T., Zapf A., and Beller M. Tetrahedron Lett. 46 (2005) 2585-2588
31. Schareina T., Zapf A., Mägerlein W., Müller N., and Beller M. Tetrahedron Lett. 48 (2007) 1087-1090
32. Schareina T., Jackstell R., Schulz T., Zapf A., Cotté A., Gotta M., and Beller M. Adv. Synth. Catal. 351 (2009) 643-648
33. In: de Vries J.G., and Elsevier C.J. (Eds). Handbook of Homogeneous Hydrogenation (2007), Wiley-VCH, Weinheim
34. In: Beller M., and Bolm C. (Eds). Transition Metals for Organic Synthesis. 2nd ed. (2004), Wiley-VCH, Weinheim
35. De Bellofon C., and Fouilloux P. Catal. Rev. 36 (1994) 459-506
36. Suarez T., and Fontal B. J. Mol. Catal. 45 (1988) 335-344
37. Joshi A.M., MacFarlane K.S., James B.R., and Frediani P. Catalysis of Organic Reacions. Chemical Industries vol. 53 (1992), Dekker, New York pp. 497-502
38. Yoshida T., Okano T., and Otsuka S. J. Chem. Soc., Chem. Commun. 19 (1979) 870-871
39. Chin C.S., and Lee B. Catal. Lett. 14 (1992) 135-140
40. Enthaler S., Addis D., Junge K., Erre G., and Beller M. Chem. Eur. J. 14 (2008) 9491-9494
41. Enthaler S., Addis D., Junge K., Erre G., and Beller M. ChemSusChem 1 (2008) 1006-1010
42. Grotevendt A., Jackstell R., Gomez M., and Beller M. ChemSusChem 2 (2009) 63-70
43. Clement N.D., Routaboul L., Grotevendt A., Jackstell R., and Beller M. Chem. Eur. J. 14 (2008) 7408-7420
44. Grotevendt A., Bartolome M., Spannenberg A., Nielsen D.J., Jackstell R., Cavell K.J., Oro L.A., and Beller M. Tetrahedron Lett. 48 (2007) 9203-9207
45. Enthaler S., Jackstell R., Hagemann B., Junge K., Erre G., and Beller M. J. Organomet. Chem. 691 (2006) 4652-4659
46. Rataboul F., Zapf A., Jackstell R., Harkal S., Riermeier T., Monsees A., Dingerdissen U., and Beller M. Chem. Eur. J. 10 (2004) 2983-2990
47. Frisch A.C., Zapf A., Briel O., Kayser B., Shaikh N., and Beller M. J. Mol. Catal. 214 (2004) 231-239
48. Seayad A.M., Selvekumar K., Moballigh A., and Beller M. Tetrahedron Lett. 44 (2003) 1679-1683
49. Frisch A.C., Shaikh N., Zapf A., and Beller M. Angew. Chem., Int. Ed. 41 (2002) 4056-4059
50. Selvakumar K., Zapf A., Spannenberg A., and Beller M. Chem. Eur. J. 8 (2002) 3901-3906
51. Selvakumar K., Zapf A., and Beller M. Org. Lett. 4 (2002) 3031-3033
52. Jackstell R., Frisch A., Beller M., Röttger D., Malaun M., and Bildstein B. J. Mol. Catal. 185 (2002) 105-112
53. Arduengo III A.J., Harlow R.L., and Kline M. J. Am. Chem. Soc. 113 (1991) 361-363
54. Arduengo III A.J. Acc. Chem. Res. 32 (1999) 913-921
55. Arduengo III A.J., Krafczyk R., Schmutzler R., Craig H.A., Goerlich J.R., Marshall W.J., and Unverzagt M. Tetrahedron 55 (1999) 14523-14534
56. For reviews see:. Diez-Gonzalez S., and Nolan S.P. Synlett (2007) 2158-2167
57. Tekavec T.N., and Louie J. Top. Organomet. Chem. 21 (2007) 159-192
58. Diez-Gonzalez S., and Nolan S.P. Top. Organomet. Chem. 21 (2007) 47-82
59. Glorius F. Top. Organomet. Chem. 21 (2007) 1-20
60. Dragutan V., Dragutan I., Delaude L., and Demonceau A. Coord. Chem. Rev. 251 (2007) 765-794
61. Kuehl O. Chem. Soc. Rev. 36 (2007) 592-607
62. Gade L., and Bellemin-Laponnaz S. Top. Organomet. Chem. 21 (2007) 117-157
63. Herrmann W.A. Angew. Chem. 114 (2002) 1342-1363
64. Selected examples:. Brown J.A., Irvine S., Kennedy A.R., Kerr W.J., Andersson S., and Nilsson G.N. Chem. Commun. (2008) 9-10
65. Bauer E.B., Andavan G.T.S., Hollis T.K., Rubio R.J., Cho J., Kuchenbeiser G.R., Helgert T.R., Letko C.S., and Tham F.S. Org. Lett. 10 (2008) 1175-1178
66. Zhang T., Wang W., Gu X., and Shi G. Organometallics 27 (2008) 753-757
67. Ben-Asuly A., Tzur E., Diesendruck C.E., Sigalov M., Goldberg I., and Lemcoff N.G. Organometallics 27 (2008) 811-813
68. Yen S.K., Koh L.L., Huynh H.V., and Hor T.S.A. Dalton Trans. 5 (2008) 699-706
69. Gao C.Y., and Yang L.M. J. Org. Chem. 73 (2008) 1624-1627
70. Marion N., de Fremont P., Puijk I.M., Ecarnot E.C., Amoroso D., Bell A., and Nolan S.P. Adv. Synth. Catal. 349 (2007) 2380-2384
71. Han Y., Huynh H.V., and Tan G.K. Organometallics 26 (2007) 6581-6585
72. Bode J.W., and Sohn S.S. J. Am. Chem. Soc. 129 (2007) 13798-13799
73. Ozdemir I., Yigit M., Yigit B., Cetinkaya B., and Cetinkaya E. J. Coord. Chem. 60 (2007) 2377-2384
74. Tu T., Assenmacher W., Peterlik H., Weisbarth R., Nieger M., and Dötz K.H. Angew. Chem., Int. Ed 46 (2007) 6368-6371
75. Vehlow K., Maechling S., and Blechert S. Organometallics 25 (2006) 25-28
76. Funk T.W., Berlin J.M., and Grubbs R.H. J. Am. Chem. Soc. 128 (2006) 1840-1846
77. Marion N., Navarro O., Mei J., Stevens E.D., Scott N.M., and Nolan S.P. J. Am. Chem. Soc. 128 (2006) 4101-4111
78. Sprengers J.W., Wassenaar J., Clement N.D., and Cavell K.J. Angew. Chem., Int. Ed. 44 (2005) 2026-2029
79. Lavallo V., Canac Y., DeHope A., Donnadieu B., and Bertrand G. Angew. Chem., Int. Ed. 44 (2005) 7236-7239
80. Altenhoff G., Goddard R., Lehmann C.W., and Glorius F. J. Am. Chem. Soc. 126 (2004) 15195-15201
81. Fürstner A., Thiel O.R., and Lehmann C.W. Organometallics 21 (2002) 331-335
82. Gómez Andreu M., Zapf A., and Beller M. Chem. Commun. (2000) 2475-2476
83. Institute of Automation (IAT), Richard Wagner Str. 31/H. 8, 18119 Rostock-Warnemünde, Germany.
84. 2] (0.0019 mmol) and the carbene ligand (0.0019 mmol) in toluene (1.0 mL) for 10 min and afterwards transferring the solution by syringe into the autoclave. Then hydrogen (35 bar) was added to the autoclave and the mixture was stirred for the respective time at 40-80 °C. After the predetermined time, the hydrogen was released and nitrobenzene or diglyme was added as internal standards. After stirring for 10 min, the reaction mixture was filtered through a short plug of silica gel. The yield was measured by GC (30 m HP Agilent Technologies column, 50-300 °C, benzonitrile: 7.08 min, benzylamine: 7.60 min).