In situ generated (Hypo)iodite catalysts for the direct α-oxyacylation of carbonyl compounds with carboxylic acids

Angewandte Chemie - International Edition

Volumn 50, Issue 23, 2011, Pages 5331-5334

  Uyanik, Muhammet ^a   Suzuki, Daisuke ^a   Yasui, Takeshi ^a   Ishihara, Kazuaki ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

cyclization; heterocycles; hypervalent compounds; iodine; oxidation

Indexed keywords

ENVIRONMENTALLY BENIGN; HETEROCYCLES; HYPERVALENT COMPOUNDS; IN-SITU; TERT-BUTYLHYDROPEROXIDE;

AMMONIUM COMPOUNDS; CARBONYL COMPOUNDS; CARBONYLATION; CARBOXYLIC ACIDS; INDUSTRIAL CHEMICALS; IODINE;

IODINE COMPOUNDS;

EID: 79957455919     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201101522     Document Type: Article

References (45)

1. P. A. Levine, A. Walti, Org. Synth. Coll. Vol. II 1943, 5.
2. Selected examples
3. J. D. Cocker, H. B. Henbest, G. H. Phillipps, G. P. Slater, D. A. Thomas, J. Chem. Soc. 1965, 6
4. M. E. Kuehne, T. C. Giacobbe, J. Org. Chem. 1968, 33, 3359
5. D. J. Rawilson, G. Sosnovsky, Synthesis 1973, 567
6. G. J. Williams, N. R. Hunter, Can. J. Chem. 1976, 54, 3830
7. T. Satoh, S. Motohashi, K. Yamakawa, Bull. Chem. Soc. Jpn. 1986, 59, 946
8. J. C. Lee, Y. S. Jin, J.-H. Choi, Chem. Commun. 2001, 956, and references therein; for the stoichiometric use of N-methyl-O-acylhydroxylamines instead of heavy metal salts, see
9. C. S. Beshara, H. Hall, R. L. Jenkins, K. L. Jones, T. C. Jones, N. M. Killeen, P. H. Taylor, S. P. Thomas, N. C. O. Tomkinson, Org. Lett. 2005, 7, 5729.
10. T. Kano, H. Mii, K. Maruoka, J. Am. Chem. Soc. 2009, 131, 3450
11. M. J. P. Vaismaa, S. C. Yau, N. C. O. Tomkinson, Tetrahedron Lett. 2009, 50, 3625
12. H. Gotoh, Y. Hayashi, Chem. Commun. 2009, 3083.
13. Recent reviews
14. R. D. Richardson, T. Wirth, Angew. Chem. 2006, 118, 4510
15. Angew. Chem. Int. Ed. 2006, 45, 4402
16. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299
17. M. Ochiai, K. Miyamoto, Eur. J. Org. Chem. 2008, 4229
18. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073
19. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086
20. L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235
21. V. V. Zhdankin, J. Org. Chem. 2011, 76, 1185.
22. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto, J. Am. Chem. Soc. 2005, 127, 12244
23. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita, Angew. Chem. 2005, 117, 6349
24. Angew. Chem. Int. Ed. 2005, 44, 6193
25. J. Sheng, X. Li, M. Tang, B. Gao, G. Huang, Synthesis 2007, 1165.
26. M. Uyanik, T. Yasui, K. Ishihara, Bioorg. Med. Chem. Lett. 2009, 19, 3848; Moriarty et al. first reported the HTIB (Koser's reagent)-promoted oxylactonization of oxocarboxylic acids 1 into oxolactones 2; see
27. R. M. Moriarty, R. K. Vaid, T. E. Hopkins, B. K. Vaid, O. Prakash, Tetrahedron Lett. 1990, 31, 201.
28. 2 or TBHP.
29. 4NBr and 70% aqueous TBHP in acetic acid at 110°C; see
30. T. Nagano, Z. Jia, X. Li, G. Liu, A. S. C. Chan, T. Hayashi, Chem. Lett. 2010, 39, 929. Notably, no reaction occurred under our milder reaction conditions using tetrabutylammonium bromide or chloride instead of tetrabutylammonium iodide as a pre-catalyst. For comparisons of our "iodine"-catalyzed oxidations with their "bromine"-catalyzed oxidations, see the Supporting Information. We previously reported our preliminary results
31. M. Uyanik, T. Yasui, K. Ishihara, Proc. 89th Ann. Meet. Jpn. Chem. Soc. 2009, 3G 3- 12
32. M. Uyanik, D. Suzuki, K. Ishihara, Proc. 90th Ann. Meet. Jpn. Chem. Soc. 2010, 3F 5- 09.
33. For details, see the Supporting Information.
34. Two selected patents
35. T. Iwamoto, H. Kitamura, T. Fujimoto, (Jpn. Kokai Tokkyo Koho), JP2009144071, July 2, 2009
36. J. Hatakeyama, S. Tachibana, Y. Osawa, (Jpn. Kokai Tokkyo Koho), JP2009169406, July 30, 2009.
37. Kirihara et al. reported the in situ generation of hypoiodite that catalyzed oxidative homocoupling of thiols to disulfides with hydrogen peroxide; see
38. M. Kirihara, Y. Asai, S. Ogawa, T. Noguchi, A. Hatano, Y. Hirai, Synthesis 2007, 3286; for selected reviews of iodine(I)-promoted reactions, see
39. A. Kirschning, H. Monenschein, W. Wittenberg, Angew. Chem. 2001, 113, 670
40. Angew. Chem. Int. Ed. 2001, 40, 650
41. A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354
42. S. Minakata, Acc. Chem. Res. 2009, 42, 1172.
43. D. Griller, K. Ingold, Acc. Chem. Res. 1980, 13, 317
44. M. Newcomb, C. C. Johnson, M. B. Manek, T. R. Varick, J. Am. Chem. Soc. 1992, 114, 10915.
45. The reaction of 9 under identical reaction conditions of Scheme 4 gave 10, but only in ≤% yield. Shim etâal. reported that 10 was obtained from a similar substrate (1,1-diphenyl-2-vinylcyclopropane) under photooxidation conditions, see:, S. C. Shim, J. S. Song, J. Org. Chem. 1986, 51, 2817. Thus, 10 might be produced from 8 and/or 9 under the reaction conditions shown in Scheme 4.