Merrifield resin-C6H4CH2N 3P(MeNCH2CH2)3N: An efficient reusable catalyst for room-temperature 1,4-addition reactions and a more convenient synthesis of its precursor P(MeNCH2CH2) 3N

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 3093-3096

  Venkat Reddy, Chinta Reddy ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NONIONIC BASE; PRODUCT YIELDS; ROOM TEMPERATURE;

ADDITION REACTIONS; BIOPOLYMERS; CATALYSTS; SYNTHESIS (CHEMICAL);

RESINS;

BASE; MERRIFIELD RESIN; POLYMER; RESIN; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYST; FILTRATION; PRECURSOR; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 34247380415     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062505z     Document Type: Article

References (62)

1. (a) Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195.
2. (b) Baker, R. T.; Kobayashi, S.; Leitner, W. Adv. Synth. Catal. 2006, 348, 1337-1340.
3. (c) Kobayashi, S.; Akiyama, R. Chem. Commun. 2003, 449-460.
4. (d) McNamara, C. A.; Dixon, M. J.; Bradley, M. 2002, 102, 3275-3300.
5. (a) Jung, M. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, UK, 1991; Vol. 4. Chapter 1. pp 1-67.
6. (b) Bensa, D.; Constantieux, T.; Rodriguez, J. Synthesis 2004, 923-927.
7. (c) Comelles, J.; Moreno-Manas, M.; Vallribera, A. ARKIVOC 2005, 9, 207-238.
8. (d) Sibi, M. P.; Manyem, S. Tetrahedron 2000, 56, 8033-8061.
9. (a) Clemens, R. J. (Eastman Kodak Co., U.S.A.), US Patent 5,017,-649, 1991; Chem. Abstr. 1991, 115, 210320.
10. (b) Nakamura, N.; Shigemori, K.; Otsuki, T.; Mashimo, Y.; Kawashima, M.; Ikeda, A.; Sato, T.; Saito, H. (Toyo Ink Manufacturing Co., Ltd., Japan), Patent WO 0116203, 2001; Chem. Abstr. 2001, 134, 208363.
11. (c) Meyer, G. R. (Nalco/Exxon Energy Chemicals, L. P., U.S.A.), US Patent 5,993,693, 1999; Chem. Abstr. 1999, 132, 14348.
12. (d) Noomen, A. Prog. Org. Coat. 1997, 32, 137-142.
13. (e) Hessler, E, J.; Amin, S. I. (Upjohn Co., U.S.A.), European Patent EP0022440, 1981; Chem. Abstr. 1981, 95, 24567.
14. (a) Garcia-Raso, A.; Garcia-Raso, J.; Campaner, B.; Mestres, R.; Sinisterra, J. V. Synthesis 1982, 1037-1041.
15. (b) Clark, J. H.; Cork, D. G.; Robertson, M. S. Chem. Lett. 1983, 1145-1148.
16. (a) Choudary, B. M.; Kavita, B.; Chowdari, N. S.; Sreedhar, B.; Kantam, M. L. Catal. Lett. 2002, 78, 373-377.
17. (b) Choudary, B. M.; Lakshmi Kantam, M.; Kavita, B.; Venkat Reddy, Ch.; Figueras, F. Tetrahedron 2000, 56, 9357-9364.
18. (c) Choudary, B. M.; Lakshmi Kantam, M.; Venkat Reddy, Ch.; Rao, K. K.; Figueras, F. J. Mol. Catal. A: Chem. 1999, 146, 279-284.
19. (d) Ebitani, K.; Motokura, K.; Mori, K.; Mizugaki, T.; Kaneda, K. J. Org. Chem. 2006, 71, 5440-5447.
20. (a) Ballini, R.; Marziali, P.; Mozzicafreddo, A. J. Org. Chem. 1996, 61, 3209-3211.
21. (b) Veldurthy, B.; Clacens, J. M.; Figueras, F. Adv. Synth. Catal. 2005, 347, 767-771.
22. (c) Prescott, H. A.; Li, Z.-J.; Kamnitz, E.; Deutsch, J.; Lieske, H. J. Mater. Chem. 2005, 15, 4616-4628.
23. (d) Ballini, R.; Bosica, G.; Livi, D.; Palmieri, A.; Maggi, R.; Sartori, G. Tetrahedron Lett. 2003, 44, 2271-2273.
24. (e) Ranu, B. C.; Subhash, B. Org. Lett. 2005, 7, 3049-3052.
25. (f) Clacens, J.-M.; Genuit, D.; Delmotte, L.; Garcia-Ruiz, A.; Bergeret, G.; Montiel, R.; Lopez, J.; Figueras, F. J. Catal. 2004, 221, 483-490.
26. (g) Zahouily, M.; Bahlaouan, B.; Aadil, M.; Rayadh, A.; Sebti, S. Org. Process Res. Dev. 2004, 8, 275-278.
27. (h) Zahouily, M.; Abrouki, Y.; Rayadh, A.; Sebti, S.; Dhimane, H.; David, M. Tetrahedron Lett. 2003, 44, 2463-2465.
28. (i) Corma, A.; Iborra, S.; Rodriguez, I.; Iglesias, M.; Sanchez, F. Catal. Lett. 2002, 82, 237-242.
29. (j) Kubota, Y.; Ikeya, H.; Sugi, Y.; Yamada, T.; Tatsumi, T. J. Mol. Catal. A: Chem. 2006, 249, 181-190.
30. (k) Xu, C.; Bartley, J. K.; Enache, D. I.; Knight, D. W.; Hutchings, G. J. Synthesis 2005, 3468-3476.
31. Ballini, R.; Fiorini, D.; Gil, M. V.; Palmieri, A. Green Chem. 2003, 475-476.
32. For recent reviews on proazaphosphatranes, see: (a) Verkade, J. G. Top. Curr. Chem. 2002, 233, 1-44.
33. (b) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2003, 59, 7819-7858.
34. (c) Verkade, J. G.; Kisanga, P. B. Aldrichimica Acta 2004, 37, 3-14.
35. (d) Urgaonkar, S.; Verkade, J. G. Spec. Chem. 2006, 26, 36-39.
36. (a) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2001, 57, 467-475.
37. (b) Kisanga, P. B.; Ilankumaran, P.; Fetterly, B. M.; Verkade, J. G. J. Org. Chem. 2002, 67, 3555-3560.
38. (c) Wroblewski, A. E.; Bansal, V.; Kisanga, P.; Verkade, J. G. Tetrahedron 2003, 59, 561-566.
39. (d) Sarkar, A.; Ilankumaran, P.; Kisanga, P.; Verkade, J. G. Adv. Synth. Catal. 2004, 346, 1093-1096.
40. (a) Ilankumaran, P.; Verkade, J. G. J. Org. Chem. 1999, 64, 9063-9066.
41. In which 4 was erroneously reported as the corresponding imine. (b) Venkat Reddy. Ch.; Fetterly, B. M.; Verkade, J. G., submitted for publication.
42. (a) Moffett, R. B. J. Am. Chem. Soc. 1957, 79, 3186-3190.
43. (b) Ho, T. L. Synth. Commun. 1982, 12, 339-341.
44. (c) Carmona, D.; Ferrer, J.; Lorenzo, M.; Lahoz, F. J.; Dobrinovitch, I. T.; Oro, L. A. Eur. J. Inorg. Chem. 2005, 9, 1657-1664.
45. (d) Rosini, G.; Maratta, E.; Ballini, R.; Petrini, M. Synthesis 1986, 237-238.
46. (e) Nakashita, Y.; Hesse, M. Helv. Chim. Acta 1983, 66, 845-860.
47. (a) Ballini, R.; Bosica, G. Eur. J. Org. Chem. 1998, 355-357.
48. (b) Wang, W.; Yu, M. Tetrahedron Lett. 2004, 45, 7141-7143.
49. (c) Bergbreiter, D. E.; Li, C. Org. Lett. 2003, 5, 2445-2447.
50. (d) Clark, J. H.; Miller, J. M.; So, K.-H. J. Chem. Soc., Perkin Trans. 1 1978, 941-946.
51. (e) Brown, R. F.; Van Gulick, N. M. J. Am. Chem. Soc. 1955, 77, 1079-1083.
52. (f) Raoult, E.; Sarrazin, J.; Tallec, A. Tetrahedron 1987, 43, 5299-5306.
53. (g) Kambe, S.; Yasuda, H. Bull. Chem. Soc. Jpn. 1966, 39, 2549-2551.
54. Bullock, W. H.; Kluender, H. C. E.; Collibee, W. L.; Dally, R.; Rodriguez, M. E.; Wang, M. Patent WO 2002020526, 2002; Chem. Abstr. 2002, 136, 247499.
55. Ono, N.; Kamimura, A.; Kaji, A. Synthesis 1984, 226-227.
56. (a) Banwell, M. G.; Edwards, A. J.; Jolliffe, K. A.; Smith, J. A.; Hamel, E.; Verdier-Pinard, P. Org. Biomol. Chem. 2003, 1, 296-305.
57. (b) Chasar, D. W. Synthesis 1982, 841-842.
58. Fetterly, B. M.; Jana, N. K.; Verkade, J. G. Tetrahedron 2006, 62, 440-456.
59. (a) Hirano, M.; Hirai, M.; Ito, Y.; Tsurumaki, T.; Baba, A.; Fukuoka, A.; Komiya, S. J. Organomet. Chem. 1998, 569, 3-14.
60. (b) Gomez-Bengoa, E.; Cuerva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553-8565.
61. (a) Schmidt, H.; Lensink, C.; Xi, S. K.; Verkade, J. G. Z. Anorg. Allg. Chem. 1989, 578, 75-80.
62. (b) Tang, J.-S.; Verkade, J. G. Tetrahedron Lett. 1993, 34, 2903-2904.