Mechanistic investigation of the one-pot formation of amides by oxidative coupling of alcohols with amines in methanol

Catalysis Today

Volumn 203, Issue , 2013, Pages 211-216

  Mielby, Jerrik ^a   Riisager, Anders ^a   Fristrup, Peter ^a   Kegnæs, Søren ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Amide formation; Gold catalysis; Hammett study; Mechanism; Oxidative coupling

Indexed keywords

AMIDE FORMATION; AMINOLYSIS; BENZYL ALCOHOL; BENZYLIC; GOLD CATALYSIS; HAMMETT PLOTS; HAMMETT STUDY; HYDRIDE ABSTRACTION; INTERMEDIATE FORMATION; METHYL ESTERS; NEGATIVE CHARGE; ONE POT; OXIDATIVE COUPLINGS; POSITIVE CHARGES; RATE DETERMINING STEP; REACTION MECHANISM; RELATIVE REACTIVITIES; SUPPORTED GOLD; TRANSITION STATE STRUCTURE; TWO-STEP MECHANISMS; TWO-STEP REACTION MECHANISMS;

AMINES; ESTERIFICATION; ESTERS; GOLD; MECHANISMS; METHANOL;

AMIDES;

EID: 84873707082     PISSN: 09205861     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cattod.2012.04.026     Document Type: Conference Paper

References (43)

1. E. Valeur, and M. Bradley Chemical Society Reviews 38 2009 606
2. M. Köhn, and R. Breinbauer Angewandte Chemie International Edition 43 2004 3106
3. J.R. Martinelli, T.P. Clark, D.A. Watson, R.H. Munday, and S.L. Buchwald Angewandte Chemie International Edition 46 2007 8460
4. W.-J. Yoo, and C.-J. Li Journal of the American Chemical Society 128 2006 13064
5. C.L. Allen, and J.M.J. Williams Chemical Society Reviews 40 2011 3405
6. C. Gunanathan, Y. Ben-David, and D. Milstein Science 317 2007 790
7. L.U. Nordstrøm, H. Vogt, and R. Madsen Journal of the American Chemical Society 130 2008 17672
8. Y. Zhang, C. Chen, S.C. Ghosh, Y. Li, and S.H. Hong Organometallics 29 2010 1374
9. S.K. Klitgaard, K. Egeblad, U.V. Mentzel, A.G. Popov, T. Jensen, E. Taarning, I.S. Nielsen, and C.H. Christensen Green Chemistry 10 2008 419
10. G.C. Bond, P.A. Sermon, G. Webb, D.A. Buchanan, and P.B. Wells Journal of the Chemical Society, Chemical Communications 1973 444b
11. G.J. Hutchings Journal of Catalysis 96 1985 292
12. M. Haruta, N. Yameda, T. Kobayashi, and S. Iijima Journal of Catalysis 115 1989 301
13. L. Prati, and M. Rossi Journal of Catalysis 176 1998 552
14. A.S.K. Hashmi, and G.J. Hutchings Angewandte Chemie International Edition 45 2006 7896
15. K.T. Højholt, A.B. Laursen, S. Kegnæs, and C.H. Christensen Topics in Catalysis 54 2011 1026
16. S. Kegnæs, J. Mielby, U.V. Mentzel, T. Jensen, P. Fristrup, and A. Riisager Chemical Communications 48 2012 2427
17. C. Marsden, E. Taarning, D. Hansen, L. Johansen, S.K. Klitgaard, K. Egeblad, and C.H. Christensen Green Chemistry 10 2008 168
18. A.B. Laursen, K.T. Højholt, S.B. Simonsen, L.F. Lundegaard, S. Helveg, F. Schüth, M. Paul, J.-D. Grunwaldt, S. Kegnæs, C.H. Christensen, and K. Egeblad Angewandte Chemie International Edition 49 2010 3504
19. Y. Wang, D. Zhu, L. Tang, and S. Wang Angewandte Chemie International Edition 50 2001 1
20. J.-F. Soulé, H. Miyamura, and S. Kobayashi Journal of the American Chemical Society 133 2011 18550
21. L.P. Hammett Journal of the American Chemical Society 59 1937 96
22. P. Fristrup, S. Le Quement, D. Tanner, and P.-O. Norrby Organometallics 23 2004 6160
23. L. Keinicke, P. Fristrup, P.-O. Norrby, and R. Madsen Journal of the American Chemical Society 127 2005 15756
24. P. Fristrup, D. Tanner, and P.-O. Norrby Chirality 15 2003 360
25. C. Hansch, A. Leo, and R. Taft Chemical Reviews 91 1991 165
26. C. Hansch, and H. Gao Chemical Reviews 97 1997 2995
27. P. Fristrup, L.B. Johansen, and C.H. Christensen Catalysis Letters 120 2007 184
28. P. Fristrup, L.B. Johansen, and C.H. Christensen Chemical Communications 2008 2750
29. S. Kegnæs, J. Mielby, U.V. Mentzel, C.H. Christensen, and A. Riisager Green Chemistry 12 2010 1437
30. A.D. Becke Journal of Chemical Physics 98 1993 5648
31. C. Lee, W. Yang, and R.G. Parr Physical Review B 37 1988 785
32. P. Fristrup, M. Kreis, A. Palmelund, P.-O. Norrby, and R. Madsen Journal of the American Chemical Society 130 2008 5206
33. J.H. Dam, P. Fristrup, and R. Madsen Journal of Organic Chemistry 73 2008 3228
34. R. Ditchfield, W.J. Hehre, and J.A. Pople Journal of Chemical Physics 54 1971 724
35. B. Marten, K. Kim, C. Cortis, R.A. Friesner, R.B. Murphy, M.N. Ringnalda, D. Sitkoff, and B. Honig Journal of Physical Chemistry 100 1996 11775
36. D.J. Tannor, B. Marten, R. Murphy, R.A. Friesner, D. Sitkoff, A. Nicholls, M. Ringnalda, W.A. Goddard III, and B. Honig Journal of the American Chemical Society 116 1994 11875
37. Continuum dielectric constant: 33.62; Solvent probe molecule radius: 2.000
38. Jaguar, version 7.8, Schrodinger, LLC, New York, NY, 2010.
39. For a discussion, see P. Fristrup, M. Ahlquist, D. Tanner, and P.-O. Norrby Journal of Physical Chemistry A 112 2008 12862
40. B. Galabov, Y. Atanasov, S. Ilieva, and H.F. Schaefer Journal of Physical Chemistry A 109 2005 11470
41. M.L. Bender Chemical Reviews 60 1960 53
42. S. Grimme Journal of Computational Chemistry 25 2004 1463
43. Y. Zhao, and D.G. Truhlar Theoretical Chemistry Accounts 120 2008 215