Esterification via iron-catalyzed activation of triphenylphosphine with air

ACS Catalysis

Volumn 1, Issue 11, 2011, Pages 1469-1474

  Taniguchi, Tsuyoshi ^a   Hirose, Daisuke ^a   Ishibashi, Hiroyuki ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

esterification; iron; oxygen; phthalocyanines; triphenylphosphine

Indexed keywords

PHTHALOCYANINES; PYRIDINE N-OXIDE; REACTION MECHANISM; TRIPHENYL PHOSPHINES; TRIPHENYLPHOSPHINE OXIDE;

CARBOXYLIC ACIDS; CATALYSIS; ESTERIFICATION; IRON; MOLECULAR OXYGEN; NITROGEN COMPOUNDS; REACTION INTERMEDIATES;

ESTERS;

EID: 80655129247     PISSN: 21555435     EISSN: None     Source Type: Journal    
DOI: 10.1021/cs2003824     Document Type: Article

References (63)

1. Valentine, D. H., Jr.; Hillhouse, J. H. Synthesis 2003, 317-334
2. Appel, R. Angew. Chem., Int. Ed. Engl. 1975, 14, 801-811
3. Bergin, E.; O?Connor, C. T.; Robinson, S. B.; McGarrigle, E. M.; O?Mahony, C. P.; Gilheany, D. G. J. Am. Chem. Soc. 2007, 129, 9566-9567
4. Mukaiyama, T. Angew. Chem., Int. Ed. Engl. 1976, 15, 94-103
5. Otera, J.; Nishikido, J. Esterification: Methods, Reactions, and Applications: Completely Revised and Enlarged, 2 nd ed.; Wiley-VCH: Weinheim, Germany, 2010; Chapter 1, pp 3-157.
6. Iranpoor, N.; Firouzabadi, H.; Khalili, D.; Motevalli, S. J. Org. Chem. 2008, 73, 4882-4887
7. Mukaiyama, T.; Kuroda, K.; Maruyama, Y. Heterocycles 2010, 80, 63-82
8. Morcillo, S. P.; Álvarez de Cienfuegos, L.; Mota, A. J.; Justicia, J.; Robles, R. J. Org. Chem. 2011, 76, 2277-2281
9. Mitsunobu, O. Synthesis 1981, 1-28
10. Hughes, D. L. Org. React. 1992, 42, 335-656
11. Kumara Swamy, K. C.; Kumar Bhuvan, N. N.; Balaraman, E.; Pavan Kumar, K. V. P. Chem. Rev. 2009, 109, 2551-2651
12. But, T. Y. S.; Lu, J.; Toy, P. H. Synlett 2010, 1115-1117
13. Stahl, S. S. Angew. Chem., Int. Ed. 2004, 43, 3400-3420
14. Punniyamurthy, T.; Velusamy, S.; Iqbal, J. Chem. Rev. 2005, 105, 2329-2364
15. Groves, J. T. In Cytochrome P450: Structure, Mechanism, and Biochemistry, 3 rd ed.; Ortiz de Montellano, P. R., Ed.; Kluwer Academic/Plenum Publishers: New York, 2005; Chapter 1, pp 1-44.
16. Costas, M.; Mehn, M. P.; Jensen, M. P.; Que, L., Jr. Chem. Rev. 2004, 104, 939-986
17. Chen, H.; Lai, W.; Shaik, S. J. Phys. Chem. B 2011, 115, 1727-1742
18. Krebs, C.; Fujimori, D. G.; Walsh, C. T.; Bollinger, J. M., Jr. Acc. Chem. Res. 2007, 40, 484-492
19. Gunay, A.; Theopold, K. H. Chem. Rev. 2010, 110, 1060-1081
20. Harischandra, D. N.; Lowery, G.; Newcomb, M. Org. Lett. 2009, 11, 2089-2092
21. Xue, G.; Hont, R. D.; Münck, E.; Que, L., Jr. Nat. Chem. 2010, 2, 400-405
22. Kotani, H.; Suenobu, T.; Lee, Y.-M.; Nam, W.; Fukuzumi, S. J. Am. Chem. Soc. 2011, 133, 3249-3251
23. Fürstner, A. Angew. Chem., Int. Ed. 2009, 48, 1364-1367
24. Sarhan, A. A.; Bolm, C. Chem. Soc. Rev. 2009, 38, 2730-2744
25. Sun, C.-L.; Li, B.-J.; Shi, Z.-J. Chem. Rev. 2011, 111, 1293-1314
26. Kim, S. O.; Sastri, C. V.; Seo, M. S.; Kim., J.; Nam, W. J. Am. Chem. Soc. 2005, 127, 4178-4179
27. Ercolani, C.; Gardini, M.; Pennesi, G.; Rossi, G. J. Mol. Catal. 1985, 30, 135-144
28. Song, X.; She, Y.; Ji, H.; Zhang, Y. Org. Process Res. Dev. 2005, 9, 297-301
29. Wu, X.-F.; Darcel, C. Eur. J. Org. Chem. 2009, 1144-1147
30. Rosa, J. N.; Reddy, R. S.; Candeias, N. R.; Cal, P. M. S. D.; Gois, P. M. Org. Lett. 2010, 12, 2686-2689
31. Petersen, T. B.; Khan, R.; Olofsson, B. Org. Lett. 2011, 13, 3462-3465
32. Berry, D. J.; DiGiovanna, C. V.; Metrick, S. S.; Murugan, R. Arkivoc 2001, 201-226
33. Xu, S.; Held, I.; Kempf, B.; Mayr, H.; Steglich, W.; Zipse, H. Chem.-Eur. J. 2005, 11, 4751-4757
34. Efimov, V. A.; Chakhmakhcheva, O. G.; Ovchinnikov, Y. A. Nucleic Acids Res. 1985, 13, 3651-3666
35. Shiina, I.; Ushiyama, H.; Yamada, Y.-k.; Kawakita, Y.-j.; Nakata, K. Chem.-Asian J. 2008, 3, 454-461
36. Weng, S.-S.; Ke, C.-S.; Chen, F.-K.; Lyu, Y.-F.; Liu, G.-Y. Tetrahedron 2011, 67, 1640-1648
37. Chin, D.-H.; La Mar, G. N.; Balch, A. L. J. Am. Chem. Soc. 1980, 102, 5945-5947
38. Vasudevan, P.; Mann, S. N.; Tyagi, S. Transition Met. Chem. 1990, 15, 81-90
39. Liao, M.-S.; Watts, J. D.; Huang, M.-J. J. Phys. Chem. A 2005, 109, 7988-8000
40. In electrochemical reduction of oxygen, it is known that Fe(Pc) has the most highly catalytic activity in several metal phthalocyanines. See: Zagal, J.; Páez, M.; Tanaka, A. A.; dos Santos, J. R., Jr.; Linkous, C. A. J. Electroanal. Chem. 1992, 339, 13-30
41. Sharma, V. B.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44, 383-386
42. Ebadi, A.; Safari, N.; Peyrovi, M. H. Appl. Catal. Gen. 2007, 321, 135-139
43. Ivšić, T.; Hameršak, Z. Tetrahedron: Asymmetry 2009, 20, 1095-1098
44. De Silva, R. R.; Ramalho, T. C.; Santos, J. M.; Figueroa-Villar, J. D. J. Phys. Chem. A 2006, 110, 1031-1040
45. Torres-Lapasió, J. R.; García-Alvarez-Coque, M. C.; Bosch, E.; Rosés, M. J. Chromatogr., A 2005, 1089, 170-186
46. Xinglong, X.; Jinlong, W.; Jialu, L.; Wei-Min, D. Synlett 2006, 2099-2103
47. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234-236
48. Hughes, D. L.; Reamer, R. A. J. Org. Chem. 1996, 61, 2967-2971
49. Capretta, A.; Laritchv, V.; Dyck, J.; Robertson, A. J. Angew. Chem., Int. Ed. 2003, 42, 4051-4054. See also ref 11
50. Mekhryakova, N. G.; Gulina, T. Y.; Li, V. D.; Bundina, N. I.; Kaliya, O. L.; Luk?yanets, E. A. Russ. J. Gen. Chem. 2001, 71, 570-590
51. Martinsen, J.; Miller, M.; Trojan, D.; Sweigart, D. A. Inorg. Chem. 1980, 19, 2162-2165
52. 2O itself might have the catalytic activity in the present reaction. See: Neu, H. M.; Zhadankin, V. V.; Nemykin, V. N. Tetrahedron Lett. 2010, 51, 6545-6548
53. Merzougui, B.; Berchadsky, Y.; Tordo, P.; Gronchi, G. Electrochim. Acta 1997, 42, 2445-2453
54. Alfassi, Z. B.; Neta, P. J. Phys. Chem. A 1997, 101, 2153-2158
55. Yasui, S.; Tojo, S.; Majima, T. Org. Biomol. Chem. 2006, 4, 2969-2973
56. Ohkubo, K.; Nanjo, T.; Fukuzumi, S. Bull. Chem. Soc. Jpn. 2006, 79, 1489-1500
57. Camp, D.; Hanson, G. R.; Jenkins, I. D. J. Org. Chem. 1995, 60, 2977-2980
58. Gupta, R.; Borovik, A. S. J. Am. Chem. Soc. 2003, 125, 13234-13242
59. Malek, A.; Latos-Grazynski, L.; Bartczak, T. J.; Zadlo, A. Inorg. Chem. 1991, 30, 3222-3230
60. Fedorova, T. M.; Topol', S. S.; Derkacheva, V. M.; Luk?yanets, E. A.; Kaliya, O. L. Russ. Chem. Bull., Int. Ed. 2004, 53) 1655-1660
61. Harvey, P. J.; von Itzstein, M.; Jenkins, I. D. Tetrahedron 1997, 53, 3933-3942
62. Shiina, I.; Miyao, R. Heterocycles 2008, 76, 1313-1328
63. Harned, A. M.; He, H. S.; Toy, P. H.; Flynn, D. L.; Hanson, P. R. J. Am. Chem. Soc. 2005, 127, 52-53