Palladium-catalyzed aminocarbonylation of aryl iodides using aqueous ammonia

Tetrahedron Letters

Volumn 54, Issue 40, 2013, Pages 5496-5499

  Xu, Tongyu ^a   Alper, Howard ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Aminocarbonylation; Aqueous ammonia; Aryl iodide; Palladium

Indexed keywords

AMMONIA; AROMATIC AMIDE; IODINE DERIVATIVE; PALLADIUM; TOLUENE;

AQUEOUS SOLUTION; ARTICLE; CARBONYLATION;

EID: 84883445506     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.07.143     Document Type: Article

References (64)

1. L. Kollár Modern Carbonylation Methods 2008 Wiley-VCH Verlag Weinheim
2. M. Beller Catalytic Carbonylation Reactions 2006 Springer Berlin
3. X.-F. Wu, H. Neumann, and M. Beller ChemSusChem 6 2013 229 241
4. X.-F. Wu, H. Neumann, and M. Beller Chem. Rev. 113 2013 1 35
5. R. Franke, D. Selent, and A. Börner Chem. Rev. 112 2012 5675 5732
6. X.-F. Wu, and H. Neumann ChemCatChem 4 2012 447 458
7. B. El Ali, and H. Alper Synlett 2000 161 171
8. T.M. Konrad, J.A. Fuentes, A.M.Z. Slawin, and M.L. Clarke Angew. Chem., Int. Ed. 49 2010 9197 9200
9. D.B.G. Williams, M.L. Shaw, M.J. Green, and C.W. Holzapfel Angew. Chem., Int. Ed. 47 2008 560 563
10. T.O. Vieira, M.J. Green, and H. Alper Org. Lett. 8 2006 6143 6145
11. W. Kim, K. Park, A. Park, J. Choe, and S. Lee Org. Lett. 15 2013 1654 1657
12. T. Kippo, K. Hamaoka, and I. Ryu J. Am. Chem. Soc. 135 2013 632 635
13. K. Takahashi, M. Yamashita, and K. Nozaki J. Am. Chem. Soc. 134 2012 18746 18757
14. R. Giri, J.K. Lam, and J.-Q. Yu J. Am. Chem. Soc. 132 2010 686 693
15. S.H. Chikkali, R. Bellini, B. de Bruin, J.I. van der Vlugt, and J.N.H. Reek J. Am. Chem. Soc. 134 2012 6607 6616
16. I. Fleischer, K.M. Dyballa, R. Jennerjahn, R. Jackstell, R. Franke, A. Spannenberg, and M. Beller Angew. Chem., Int. Ed. 52 2013 2949 2953
17. J. Ferguson, F. Zeng, and H. Alper Org. Lett. 14 2012 5602 5605
18. N. Hasegawa, V. Charra, S. Inoue, Y. Fukumoto, and N. Chatani J. Am. Chem. Soc. 133 2011 8070 8073
19. A. Brennführer, H. Neumann, and M. Beller Angew. Chem., Int. Ed. 48 2009 4114 4133
20. X.-F. Wu, H. Neumann, and M. Beller Chem. Soc. Rev. 40 2011 4986 5009
21. G. Kiss Chem. Rev. 101 2001 3435 3456
22. A. Brennführer, H. Neumann, and M. Beller ChemCatChem 1 2009 28 41
23. K.M. Driller, S. Prateeptongkum, R. Jackstell, and M. Beller Angew. Chem., Int. Ed. 50 2011 537 541
24. K.M. Driller, H. Klein, R. Jackstell, and M. Beller Angew. Chem., Int. Ed. 48 2009 6041 6044
25. K.S. Bloome, and E.J. Alexanian J. Am. Chem. Soc. 132 2010 12823 12825
26. X.-F. Wu, H. Neumann, A. Spannenberg, T. Schulz, H. Jiao, and M. Beller J. Am. Chem. Soc. 132 2010 14596 14602
27. S.-M. Lu, and H. Alper J. Am. Chem. Soc. 127 2005 14776 14784
28. W. Yuan, X. Dong, M. Shi, P. McDowell, and G. Li Org. Lett. 14 2012 5582 5585
29. T.M. Gøgsig, R.H. Taaning, A.T. Lindhardt, and T. Skrydstrup Angew. Chem., Int. Ed. 51 2012 798 801
30. Y. Li, D. Xue, C. Wang, Z.-T. Liu, and J. Xiao Chem. Commun. 2012 1320 1322
31. H. Cao, T.O. Vieira, and H. Alper Org. Lett. 13 2011 11 13
32. F. Zeng, and H. Alper Org. Lett. 12 2010 5567 5569
33. V.R. Pattabiraman, and J.W. Bode Nature 480 2011 471 479
34. T. Cupido, J. Tulla-Puche, J. Spengler, and F. Albericio Curr. Opin. Drug Discovery Dev. 10 2007 768 783
35. J.M. Humphrey, and A.R. Chamberlin Chem. Rev. 97 1997 2243 2266
36. C.L. Allen, and J.M.J. Williams Chem. Soc. Rev. 40 2011 3405 3415
37. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606 631
38. D.J.C. Constable, P.J. Dunn, J.D. Hayler, G.R. Humphrey, J.L. Leazer Jr., R.J. Linderman, K. Lorenz, J. Manley, B.A. Pearlman, A. Wells, A. Zaks, and T.Y. Zhang Green Chem. 9 2007 411 420
39. C.A.G.N. Montalbetti, and V. Falque Tetrahedron 61 2005 10827 10852
40. S.-Y. Han, and Y.-A. Kim Tetrahedron 60 2004 2447 2467
41. A. Schoenberg, I. Bartoletti, and R.F. Heck J. Org. Chem. 39 1974 3318 3326
42. A. Schoenberg, and R.F. Heck J. Org. Chem. 39 1974 3327 3331
43. A. Schoenberg, and R.F. Heck J. Am. Chem. Soc. 96 1974 7761 7764
44. S. Roy, S. Roy, and G.W. Gribble Tetrahedron 68 2012 9867 9923
45. C.F.J. Barnard Organometallics 27 2008 5402 5422
46. J.R. Martinelli, D.A. Watson, D.M.M. Freckmann, T.E. Barder, and S.L. Buchwald J. Org. Chem. 73 2008 7102 7107
47. J.R. Martinelli, D.M.M. Freckmann, and S.L. Buchwald Org. Lett. 8 2006 4843 4846
48. J.R. Martinelli, T.P. Clark, D.A. Watson, R.H. Munday, and S.L. Buchwald Angew. Chem., Int. Ed. 46 2007 8460 8463
49. E. Morera, and G. Ortar Tetrahedron Lett. 39 1998 2835 2838
50. A. Schnyder, M. Beller, G. Mehltretter, T. Nsenda, and M. Studer Indolese, A. F J. Org. Chem. 66 2001 4311 4315
51. K. Hosoi, K. Nozaki, and T. Hiyama Org. Lett. 4 2002 2849 2851
52. D.N. Sawant, Y.S. Wagh, K.D. Bhatte, and B.M. Bhanage J. Org. Chem. 76 2011 5489 5494
53. Y. Wan, M. Alterman, M. Larhed, and A.J. Hallberg Comb. Chem. 5 2003 82 84
54. E. Takács, C. Varga, R. Skoda-Földesa, and L. Kollár Tetrahedron Lett. 48 2007 2453 2456
55. X. Wu, J. Wannberg, and M. Larhed Tetrahedron 62 2006 4665 4670
56. K. Ueda, Y. Sato, and M. Mori J. Am. Chem. Soc. 122 2000 10722 10723
57. D.U. Nielsen, R.H. Taaning, A.T. Lindhardt, T.M. Gøgsig, and T. Skrydstrup Org. Lett. 13 2011 4454 4457
58. P.G. Alsabeh, M. Stradiotto, H. Neumann, and M. Beller Adv. Synth. Catal. 354 2012 3065 3070
59. X.-F. Wu, H. Neumann, and M. Beller Chem. Asian J. 5 2010 2168 2172
60. X.-F. Wu, H. Neumann, and M. Beller Chem. Eur. J. 16 2010 9750 9753
61. X.-F. Wu, H. Neumann, and M. Beller Chem. Eur. J. 18 2012 419 422
62. X.-F. Wu, J. Schranck, H. Neumann, and M. Beller ChemCatChem 4 2012 69 71
63. Q. Yang, H. Cao, A. Robertson, and H. Alper J. Org. Chem. 75 2010 6297 6299
64. J. McNulty, J.J. Nair, and A. Capretta Tetrahedron Lett. 50 2009 4087 4091