Selective palladium-catalyzed aminocarbonylation of olefins with aromatic amines and nitroarenes

Angewandte Chemie - International Edition

Volumn 52, Issue 52, 2013, Pages 14089-14093

  Fang, Xianjie ^a   Jackstell, Ralf ^a   Beller, Matthias ^a  

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

Author keywords

alkenes; amides; aminocarbonylation; aromatic amines; nitroarenes

Indexed keywords

AMINOCARBONYLATION; AROMATIC AMINES; ATOM-EFFICIENT; FUNCTIONALIZATIONS; NITROARENES; PALLADIUM-CATALYZED; PD-BASED CATALYST;

AMIDES; OLEFINS;

AMINES;

EID: 84890664637     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201308455     Document Type: Article

References (61)

1. X.-F. Wu, H. Neumann, M. Beller, Chem. Rev. 2013, 113, 1
2. X.-F. Wu, H. Neumann, M. Beller, Chem. Soc. Rev. 2011, 40, 4986
3. J. Hartwig, in Organotransition Metal Chemistry, University Science Books, Sausalito, CA, 2010, pp. 745-824
4. Modern Carbonylation Methods (Ed.:, L. Kollár,), Wiley-VCH, Weinheim, 2008
5. Catalytic Carbonylation Reactions (Ed.:, M. Beller,), Springer, Berlin, 2006
6. Applied Homogeneous Catalysis with Organometallic Compounds (Eds.:, B. Cornils, W. A. Herrmann,), Wiley-VCH, Weinheim, 2002.
7. B. ElAli, H. Alper, M. Beller, C. Bolm, in Transition Metals for Organic Synthesis, Wiley-VCH, Weinheim, 2008, pp. 49-67
8. G. Kiss, Chem. Rev. 2001, 101, 3435
9. A. Brennführer, H. Neumann, M. Beller, ChemCatChem 2009, 1, 28.
10. W. Reppe, H. Vetter, Justus Liebigs Ann. Chem. 1953, 582, 133
11. T. M. Konrad, J. A. Fuentes, A. M. Z. Slawin, M. L. Clarke, Angew. Chem. 2010, 122, 9383
12. Angew. Chem. Int. Ed. 2010, 49, 9197
13. A. J. Rucklidge, G. E. Morris, A. M. Z. Slawin, D. J. Cole-Hamilton, Helv. Chim. Acta 2006, 89, 1783
14. B. C. Zhu, X. Z. Jiang, Appl. Organomet. Chem. 2006, 20, 277
15. J. Gironès, J. Duran, A. Polo, J. Real, Chem. Commun. 2003, 1776
16. G. R. Eastham, M. Waugh, P. Pringle, T. P. W. Turner, WO2011083305, 2011
17. C. Jiménez-Rodriguez, G. R. Eastham, D. J. Cole-Hamilton, Inorg. Chem. Commun. 2005, 8, 878
18. A. A. Núñez Magro, L.-M. Robb, P. J. Pogorzelec, A. M. Z. Slawin, G. R. Eastham, D. J. Cole-Hamilton, Chem. Sci. 2010, 1, 723.
19. R. Chinchilla, C. Nájera, Chem. Rev. 2013, DOI
20. "Recent Developments in Alkyne Carbonylation":, S. Doherty, J. G. Knight, C. H. Smyth, in Modern Carbonylation Methods (Ed.:, L. Kollár,), Wiley-VCH, Weinheim, 2008.
21. B. El Ali, K. Okuro, G. Vasapollo, H. Alper, J. Am. Chem. Soc. 1996, 118, 4264
22. K. Okuro, H. Kai, H. Alper, Tetrahedron: Asymmetry 1997, 8, 2307
23. C. Dong, H. Alper, Tetrahedron: Asymmetry 2004, 15, 35.
24. For reviews, see, A. Brennführer, H. Neumann, M. Beller, Angew. Chem. 2009, 121, 4176
25. Angew. Chem. Int. Ed. 2009, 48, 4114; recent examples
26. X.-F. Wu, J. Schranck, H. Neumann, M. Beller, ChemCatChem 2012, 4, 69
27. X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 419
28. X.-F. Wu, H. Neumann, M. Beller, Chem. Eur. J. 2012, 18, 9750
29. D. C. Reeves, S. Rodriguez, H. Lee, N. Haddad, D. Krishnamurthy, C. H. Senanayake, Org. Lett. 2011, 13, 2495
30. P. Hermange, A. T. Lindhardt, R. H. Tanning, K. Bjerglund, D. Lupp, T. Skrydstrup, J. Am. Chem. Soc. 2011, 133, 6061
31. D. U. Nielsen, K. Neumann, R. H. Tanning, A. T. Lindhardt, A. Modvig, T. Skrydstrup, J. Org. Chem. 2012, 77, 6155.
32. J. M. Humphrey, A. R. Chamberlin, Chem. Rev. 1997, 97, 2243
33. T. Cupido, J. Tulla-Puche, J. Spengler, F. Albericio, Curr. Opin. Drug Discovery Dev. 2007, 10, 768
34. C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405
35. V. R. Pattabiraman, J. W. Bode, Nature 2011, 480, 471.
36. P. Pino, R. Magri, Chim. Ind. 1952, 34, 511
37. P. Pino, P. Paleari, Gazz. Chim. Ital. 1951, 81, 64
38. N. S. Imyanitov, D. M. Rudkvsku, Chem. Abstr. 1967, 66, 10530
39. B. F. Crowe, O. C. Elmer, Chem. Abstr. 1956, 50, 16849
40. B. K. Nefedov, N. S. Sergeeva, Ya. T. Eidus, Chem. Abstr. 1975, 83, 205731.
41. W. Reppe, H. Kroper, Ger. Pat. 1951, 149, 868
42. W. Reppe, H. Main, Chem. Abstr. 1953, 47, 5428.
43. A. Striegler, J. Weber, J. Prakt. Chem. 1965, 29, 281.
44. T. J. Kealy, R. E. Benson, J. Org. Chem. 1961, 26, 3126.
45. Y. Tsuji, T. Ohsumi, T. Kondo, Y. Watanabe, J. Organomet. Chem. 1986, 309, 333.
46. S. I. Lee, S. U. Son, Y. K. Chung, Chem. Commun. 2002, 1310.
47. R. Jennerjahn, I. Piras, R. Jackstell, R. Franke, K.-D. Wiese, M. Beller, Chem. Eur. J. 2009, 15, 6383
48. X. Fang, M. Zhang, R. Jackstell, M. Beller, Angew. Chem. 2013, 125, 4743
49. Angew. Chem. Int. Ed. 2013, 52, 4645.
50. V. V. Grushin, Chem. Rev. 1996, 96, 2011
51. R. P. Tooze, K. Whiston, A. P. Malyan, M. J. Taylor, N. W. Wilson, J. Chem. Soc. Dalton Trans. 2000, 3441
52. A. Seayad, S. Jayasree, K. Damodaran, L. Toniolo, R. V. Chaudhari, J. Organomet. Chem. 2000, 601, 100.
53. E. Drent, P. H. M. Budzelaar, J. Organomet. Chem. 2000, 593-594, 211
54. G. R. Eastham, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. Zacchini, Chem. Commun. 2000, 609
55. W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, S. J. Zacchini, Chem. Soc. Dalton Trans. 2002, 3300
56. P. W. N. M. van Leeuwen, M. A. Zuideveld, B. H. G. Swennenhuis, Z. Freixa, P. C. J. Kamer, K. Goubitz, J. Fraanje, M. Lutz, A. L. Spek, J. Am. Chem. Soc. 2003, 125, 5523
57. J. J. R. Frew, K. Damian, H. Van Rensburg, A. M. Z. Slawin, R. P. Tooze, M. L. Clarke, Chem. Eur. J. 2009, 15, 10504
58. P. Roesle, C. J. Dürr, H. M. Möller, L. Cavallo, L. Caporaso, S. Mecking, J. Am. Chem. Soc. 2012, 134, 17696
59. R. Suleiman, J. Tijani, B. ElAli, Appl. Organomet. Chem. 2010, 24, 38.
60. F. Korodi, Z. Cziaky, Org. Prep. Proced. Int. 1990, 22, 579
61. T. P. Blackburn, B. Cox, A. J. Guildford, D. J. Le Count, D. N. Middlemiss, R. J. Pearce, C. W. Thornber, J. Med. Chem. 1987, 30, 2252.