Direct allylic amination of allylic alcohols with aromatic/aliphatic amines using Pd/TPPTS as an aqueous phase recyclable catalyst

Catalysis Science and Technology

Volumn 2, Issue 4, 2012, Pages 835-840

  Wagh, Yogesh S ^a   Sawant, Dinesh N ^a   Dhake, Kishor P ^a   Bhanage, Bhalchandra M ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL AMINE; ALLYLIC ALCOHOL; ALLYLIC AMINATION; AQUEOUS MEDIUM; AQUEOUS PHASE; CHEMOSELECTIVE; COCATALYST; DIRECT ACTIVATION; FUNCTIONALIZED; RECYCLABLE CATALYST; WATERSOLUBLE;

CATALYSTS;

AMINES;

EID: 84859369643     PISSN: 20444753     EISSN: 20444761     Source Type: Journal    
DOI: 10.1039/c2cy00474g     Document Type: Article

References (53)

1. J. Tsuji, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed., E.-i. Negishi, John Wiley & Sons, Inc., New York, USA, 2003, vol. 2, ch 1.1
2. Comprehensive Organic Synthesis, ed., B. M. Trost, and, I. Fleming, Pergamon, New York, 1991, vol. 4, p. 585
3. C. Torborg M. Beller Adv. Synth. Catal. 2009 351 3027 3043
4. M. Prashad J. Med. Chem. 1993 36 631 632
5. E. T. Michalson J. Szmuszkovicz Prog. Drug Res. 1989 22 135 149
6. G. Petranyi N. S. Ryder A. Stutz Science 1984 224 1239 1241
7. B. M. Trost M. L. Crawley Chem. Rev. 2003 103 2921 2943
8. T. E. Muller K. C. Hultzsch M. Yus F. Foubelo M. Tada Chem. Rev. 2008 108 3795 3892
9. I. Kadota A. Shibuya L. M. Lutete Y. Yamamoto J. Org. Chem. 1999 64 4570 4571
10. N. T. Patil H. Wu I. Kadota Y. Yamamoto J. Org. Chem. 2004 69 8745 8750
11. Y. S. Wagh P. J. Tambade D. N. Sawant B. M. Bhanage Eur. J. Org. Chem. 2010 5071 5076
12. Y. S. Wagh D. N. Sawant P. J. Tambade K. P. Dhake B. M. Bhanage Tetrahedron 2011 67 2414 2421
13. K. E. Atkins W. E. Walker R. M. Manyik Tetrahedron Lett. 1970 3821 3824
14. S.-C. Yang Y.-C. Tsai Organometallics 2001 20 763 770
15. H. Kinoshita H. Shinokubo K. Oshima Org. Lett. 2004 6 4085 4088
16. S.-C. Yang Y.-C. Hsu K.-H. Gan Tetrahedron 2006 62 3949 3958
17. T. Nishikata B. H. Lipshutz Org. Lett. 2009 11 2377 2379
18. D. Xing D. Yang Org. Lett. 2010 12 1068 1071
19. P. Mukherjee R. A. Widenhoefer Org. Lett. 2010 12 1184 1187
20. P. Mukherjee R. A. Widenhoefer Org. Lett. 2011 13 1334 1337
21. S.-C. Yang W.-H. Feng K.-H. Gan Tetrahedron 2006 62 3752 3760
22. M. Utsunomiya Y. Miyamoto J. Ipposhi T. Ohshima K. Mashima Org. Lett. 2007 9 3371 3374
23. T. Ohshima Y. Miyamoto J. Ipposhi Y. Nakahara M. Utsunomiya K. Mashima J. Am. Chem. Soc. 2009 131 14317 14328
24. I. Dubovyk I. D. G. Watson A. K. Yudin J. Am. Chem. Soc. 2007 129 14172 14173
25. L. Adak K. Chattopadhyay B. C. Ranu J. Org. Chem. 2009 74 3982 3985
26. T. Nagano S. Kobayashi J. Am. Chem. Soc. 2009 131 4200 4201
27. M.-C. Liao X.-H. Duan Y.-M. Liang Tetrahedron Lett. 2005 46 3469 3472
28. H. Danjo D. Tanaka T. Hayashi Y. Uozumi Tetrahedron 1999 55 14341 14352
29. M. Feuerstein D. Laurenti H. Doucet M. Santelli Tetrahedron Lett. 2001 42 2313 2315
30. Y. Uozumi H. Tanaka K. Shibatomi Org. Lett. 2004 6 281 283
31. T. Nishikata B. H. Lipshutz Chem. Commun. 2009 6472 6474
32. M. Moreno-Manas L. Morral R. Pleixats J. Org. Chem. 1998 63 6160 6166
33. K. H. Shaughnessy Chem. Rev. 2009 109 643 710
34. U. M. Lindstrom Chem. Rev. 2002 102 2751 2772
35. A. N. Marziale D. Jantke S. H. Faul T. Reiner E. Herdtweck J. Eppinger Green Chem. 2011 13 169 177
36. D. B. Bagal Z. S. Qureshi K. P. Dhake S. R. Khan B. M. Bhanage Green Chem. 2011 13 1490 1494
37. S. Shirakawa S. Shimizu Synlett 2008 1539 1542
38. H. Gulyas A. Szolloosy B. E. Hanson J. Bakos Tetrahedron Lett. 2002 43 2543 2546
39. V. Michelet, M. Savignac and J.-P. Genet, Electronic Encyclopedia of Reagents for Organic Synthesis, John Wiley, New York, 2004
40. L. Leseurre, J.-P. Genet and V. Michelet, in Handbook of Green Chemistry Series: Water as a Green Solvent, ed., P. Anastas, and, C.-J. Li, John Wiley and Sons, 2010, ch. 5
41. J. P. Genet, M. Savignac and S. Lemaire-Audoire, in Chemistry for the 21st century IUPAC Monographs, ed., S. I. Murahashi, and, S. G. Davies, New York, 1999, pp. 55-79
42. B. M. Bhanage S. S. Divekar R. M. Deshpande R. V. Chaudhari Org. Process Res. Dev. 2000 4 342 345
43. H. Shaughnessy Eur. J. Org. Chem. 2006 1827 1835
44. F. Neatu L. Protesescu M. Florea V. I. Parvulescu C. M. Teodorescu N. Apostol P. Y. Toullec V. Michelet Green Chem. 2010 12 2145 2149
45. E. Blart J. P. Genet M. Safi M. Savignac D. Sinou Tetrahedron 1994 50 505 514
46. S. Sigismondi D. Sinou J. Mol. Catal. A: Chem. 1997 116 289 296
47. A. Choplin S. dos Santos F. Quignard S. Sigismondi D. Sinou Catal. Today 1998 42 471 478
48. S. Santos Y. Tong F. Quignard A. Choplin D. Sinou J. P. Dutasta Organometallics 1998 17 78 89
49. J. P. Genet E. Blart M. Savignac Synlett 1992 715 717
50. J. P. Genet E. Blart M. Savignac S. Lemeune S. Lemaire-Audoire J.-M. Paris J.-M. Bernard Tetrahedron 1994 50 497 503
51. J. P. Genet M. Savignac J. Organomet. Chem. 1999 576 305 317
52. C. Amatore E. Blart J. P. Genet A. Jutand S. Lemaire-Audoire M. Savignac J. Org. Chem. 1995 60 6829 6839
53. C.-J. Li Acc. Chem. Res. 2002 35 533 538