Polymer-mounted N3=P(MeNCH2CH2) 3N: A green, efficient and recyclable catalyst for room-temperature transesterifications and amidations of unactivated esters

Tetrahedron Letters

Volumn 52, Issue 49, 2011, Pages 6523-6529

  Chintareddy, Venkat Reddy ^a   Ho, Hung An ^a   Sadow, Aaron D ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Amidation; Azidoproazaphosphatrane; Merrifield resin; Reusability; Solid supported catalyst; Transesterification

Indexed keywords

BENZYL ESTER; ESTER; ETHYL ESTER; GLYCERYL ESTER; GLYCERYL TRIBENZOATE; METHANOL; METHYL ESTER; POLYMER; RESIN; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SYNTHESIS; TRANSESTERIFICATION;

EID: 80555149297     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.102     Document Type: Article

References (64)

1. S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, and S.J. Taylor J. Chem. Soc., Perkin Trans. 1 2000 3815 4195
2. R.T. Baker, S. Kobayashi, and W. Leitner Adv. Synth. Catal. 348 2006 1337 1340
3. S. Kobayashi, and R. Akiyama Chem. Commun. 2003 449 460
4. C.A. McNamara, M.J. Dixon, and M. Bradley Chem. Rev. 102 2002 3275 3300
5. N.E. Leadbeater, and M. Marco Chem. Rev. 102 2002 3217 3274
6. D.H. Drewry, D.M. Coe, and S. Poon Med. Res. Rev. 19 1999 97 148
7. J. Otera Chem. Rev. 93 1993 1449 1470
8. V. Nair, S. Bindu, and V. Sreekumar Angew. Chem., Int. Ed. 43 2004 5130 5135
9. G.A. Grasa, R. Singh, and S.P. Nolan Synthesis 2004 971 985
10. J. Otera Acc. Chem. Res. 37 2004 288 296
11. M. Toda, A. Takagaki, M. Okamura, J.N. Kondo, S. Hayashi, K. Domen, and M. Hara Nature 438 2005 178
12. G. Knothe Fuel Process. Technol. 86 2005 1059 1070
13. E. Lotero, Y. Liu, D.E. Lopez, A. Suwannakaran, D.A. Bruce, and J.G. Goodwin Jr. Ind. Eng. Chem. Res. 44 2005 5353 5363
14. C. Venkat Reddy, R. Oshel, and J.G. Verkade Energy Fuels 20 2006 1310 1314
15. H.E. Hoydonckx, D.E. De Vos, S.A. Chavan, and P.A. Jacobs Top. Catal. 27 2004 83 96
16. H. Yazawa, K. Tanaka, and K. Kariyone Tetrahedron Lett. 1974 3995 3996
17. M. Brenner, and W. Huber Helv. Chem. Acta 36 1953 1109 1115
18. C.E. Rehberg, and C.H. Fisher J. Am. Chem. Soc. 66 1944 1203 1207
19. C.E. Rehberg, W.A. Faucette, and C.H. Fisher J. Am. Chem. Soc. 66 1944 1723 1724
20. C.E. Rehberg Organic Synthesis Collective Vol. 3 1955 Wiley New York pp 146-148
21. J.K. Haken J. Appl. Chem. 13 1963 168 171
22. R.W. Taft Jr., M.S. Newman, and F.H. Verhoek J. Am. Chem. Soc. 72 1950 4511 4519
23. J.H. Billman, W.T. Smith Jr., and J.L. Rendall J. Am. Chem. Soc. 69 1947 2058 2059
24. L. Osipow, F.D. Snell, W.C. York, and A. Finchler Ind. Eng. Chem. 48 1956 1459 1462
25. L. Osipow, F.D. Snell, and A. Finchler J. Am. Oil Chem. Soc. 34 1957 185 188
26. S. Komori, M. Okahara, and K. Okamoto J. Am. Oil Chem. Soc. 37 1960 468 473
27. G.A. Grasa, T. Guveli, R. Singh, and S.P. Nolan J. Org. Chem. 68 2003 2812 2819
28. G.W. Nyce, J.A. Lamboy, E.F. Connor, R.M. Waymouth, and J.L. Hedrick Org. Lett. 4 2002 3587 3590
29. R. Singh, R.M. Kissling, M.-A. Letellier, and S.P. Nolan J. Org. Chem. 69 2004 209 212
30. G.A. Grasa, R.M. Kissling, and S.P. Nolan Org. Lett. 4 2002 3583 3586
31. D.-W. Yoo, J.-H. Han, S.H. Nam, H.J. Kim, C. Kim, and J.-K. Lee Inorg. Chem. Commun. 9 2006 654 657
32. X. Hao, A. Yoshida, and J. Nishikido Tetrahedron Lett. 45 2004 781 785
33. D.E. Ponde, V.H. Deshpande, V.J. Bulbule, A. Sudalai, and A.S. Gajare J. Org. Chem. 63 1998 1058 1063
34. B.M. Choudary, M.L. Kantam, C. Venkat Reddy, S. Aranganathan, P.L. Shanti, and F. Figueras J. Mol. Catal. A: Chem. 159 2000 411 416
35. A. Solhy, J.H. Clark, R. Tahir, S. Sebtic, and M. Larzek Green Chem. 8 2006 871 874
36. F. Bazi, H.E. Badaoui, S. Samira Sokori, S. Tamani, M. Hamza, S. Boulaajaj, and S. Sebti Synth. Commun. 36 2006 1585 1592
37. M.L. Kantam, V. Neeraja, B. Bharathi, and C. Venkat Reddy Catal. Lett. 62 1999 67 69
38. B.C. Ranu, P. Dutta, and A. Sarkar J. Org. Chem. 63 1998 6027 6028
39. P. Baumhof, R. Mazitschek, and A. Giannis Angew. Chem., Int. Ed. 40 2001 3672 3674
40. J. Xiang, S. Toyoshima, A. Orita, and J. Otera Angew. Chem., Int. Ed. 40 2001 3670 3672
41. S.B. Bose, A. Satyender, A.P. Rudra Das, and H.B. Mereyala Synthesis 2006 2392 2396
42. K.V.N.S. Srinivas, I. Mahender, and B. Das Synthesis 2003 2479 2482
43. For reviews on applications of proazaphosphatranes in synthetic organic chemistry, see: J.G. Verkade Top. Curr. Chem. 233 2002 1 44
44. P.B. Kisanga, and J.G. Verkade Tetrahedron 59 2003 7819 7858
45. J.G. Verkade, and P.B. Kisanga Aldrichim. Acta 37 2004 3 14
46. Urgaonkar, S.; Verkade, J. G. "Proazaphosphatrane Catalysts for Key Industrial Reactions" Speciality Chemicals 2006, 26, 36-39.
47. References for proazaphosphatranes as electron-rich bulky ligands in cross-coupling reactions include: W. Su, S. Urgaonkar, P.A. McLaughlin, and J.G. Verkade J. Am. Chem. Soc. 126 2004 16433 16439
48. J. You, and J.G. Verkade Angew. Chem., Int. Ed. 42 2003 5051 5054
49. S. Urgaonkar, and J.G. Verkade Adv. Synth. Catal. 346 2004 611 616
50. C. Venkat Reddy, S. Urgaonkar, and J.G. Verkade Org. Lett. 7 2005 4427 4430
51. S. Urgaonkar, M. Nagarajan, and J.G. Verkade Tetrahedron Lett. 43 2002 8921 8924
52. P. Ilankumaran, and J.G. Verkade J. Org. Chem. 64 1999 3086 3089
53. A. Sarkar, P. Ilankumaran, P. Kisanga, and J.G. Verkade Adv. Synth. Catal. 346 2004 1093 1096
54. P. Ilankumaran, and J.G. Verkade J. Org. Chem. 64 1999 9063 9066 in which 4 was erroneously reported as the corresponding imine
55. 19a except that the temperature employed was 70 °C rather than 130 °C, See C. Venkat Reddy, B.M. Fetterly, and J.G. Verkade Energy Fuels 21 2007 2466 2472 This manuscript also reports the crystal structure of small molecule analogs of polymer catalyst 4
56. The precursor (1) for the synthesis of polymer catalyst 4 was synthesized using our modified procedure C. Venkat Reddy, and J.G. Verkade J. Org. Chem. 72 2007 3092 3096 The polymer catalyst 5 was prepared analogously to 4 except that FibreCat was used as the starting material in stead of Merrifield resin
57. M. Movassaghi, and M.A. Schmidt Org. Lett. 7 2005 2453 2456 and references cited therein
58. G. Benz B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 6 1991 Pergamon Press Oxford Chapter 2.3
59. F. Albericio, R. Chinchilla, D.J. Dodsworth, and C. Najera Org. Prep. Proceed. Int. 33 2001 203 303
60. P. Wipf Chem. Rev. 95 1995 2115 2134
61. Z. Jin Nat. Prod. Rep. 20 2003 584 605
62. C. Sabot, K.A. Kumar, S. Meunier, and C. Mioskowski Tetrahedron Lett. 48 2007 3863 3866
63. For electrochemical amidation of esters, see: K. Arai, C.H. Shaw, K. Nozawa, K. Kawai, and S. Nakajima Tetrahedron Lett. 28 1987 441 442
64. A.P. Phillips J. Am. Chem. Soc. 73 1951 5557 5559