Catalysis with InSitu-Generated (Hypo)iodite Ions for Oxidative Coupling Reactions

ChemCatChem

Volumn 4, Issue 2, 2012, Pages 177-185

  Uyanik, Muhammet ^a   Ishihara, Kazuaki ^a,b  

^a NAGOYA UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Chemoselectivity; Homogeneous catalysis; Hydrogen peroxide; Iodine; Oxidative coupling; TBHP

Indexed keywords

CATALYTIC SYSTEM; CHEMO-SELECTIVITY; ENVIRONMENTALLY BENIGN; HOMOGENEOUS CATALYSIS; IN-SITU; OXIDATIVE COUPLING REACTIONS; OXIDATIVE COUPLINGS; REACTION CONDITIONS; TBHP; TERT-BUTYL ALCOHOLS; TERT-BUTYLHYDROPEROXIDE;

ALCOHOLS; CATALYSIS; CATALYTIC OXIDATION; FUNCTIONAL GROUPS; HYDROGEN PEROXIDE; IODINE; REACTION KINETICS;

IONS;

EID: 84859603895     PISSN: 18673880     EISSN: 18673899     Source Type: Journal    
DOI: 10.1002/cctc.201100352     Document Type: Article

References (79)

1. P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123;
2. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2002, 102, 2523;
3. Hypervalent Iodine Chemistry, T. Wirth (Ed. ), Top. Curr. Chem. 2003, 224
4. V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299;
5. U. Ladziata, V. V. Zhdankin, Arkivoc 2006, 26;
6. V. V. Zhdankin, Arkivoc 2009, 1;
7. E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214; Angew. Chem. Int. Ed. 2009, 48, 9052;
8. L. Pouységu, D. Deffieux, S. Quideau, Tetrahedron 2010, 66, 2235;
9. V. V. Zhdankin, J. Org. Chem. 2011, 76, 1185.
10. Selected reviews:
11. R. D. Richardson, T. Wirth, Angew. Chem. 2006, 118, 4510; Angew. Chem. Int. Ed. 2006, 45, 4402;
12. M. Ochiai, K. Miyamoto, Eur. J. Org. Chem. 2008, 4229;
13. T. Dohi, Y. Kita, Chem. Commun. 2009, 2073;
14. M. Uyanik, K. Ishihara, Chem. Commun. 2009, 2086.
15. M. Ochiai, Y. Takeuchi, T. Katayama, T. Sueda, K. Miyamoto, J. Am. Chem. Soc. 2005, 127, 12244;
16. T. Dohi, A. Maruyama, M. Yoshimura, K. Morimoto, H. Tohma, Y. Kita, Angew. Chem. 2005, 117, 6349; Angew. Chem. Int. Ed. 2005, 44, 6193.
17. Selected reviews:
18. J.-P. Lang in Encyclopedia of Inorganic Chemistry, 2nded., Vol.II (Ed: R.B. King), Wiley, New York, 2005, pp.866-887;
19. A. G. Wee, J. Slobodian, N. A. Fernández-Rodríguez, E. Aguilar in Encyclopedia of Reagents for Organic Synthesis, 2nded., Vol.11 (Eds: L.A. Paquette, D. Crich, P.L. Fuchs, G.A. Molander), Wiley, Chichester, 2009, pp.8921-8930.
20. Selected reviews:
21. A. Kirschning, H. Monenschein, W. Wittenberg, Angew. Chem. 2001, 113, 670; Angew. Chem. Int. Ed. 2001, 40, 650;
22. A. N. French, S. Bissmire, T. Wirth, Chem. Soc. Rev. 2004, 33, 354;
23. S. Minakata, Acc. Chem. Res. 2009, 42, 1172.
24. M. Kirihara, Y. Asai, S. Ogawa, T. Noguchi, A. Hatano, Y. Hirai, Synthesis 2007, 3286.
25. M. Uyanik, H. Okamoto, T. Yasui, K. Ishihara, Science 2010, 328, 1376;
26. M. Uyanik, K. Ishihara, Chim. Oggi 2011, 29, 18.
27. M. Uyanik, D. Suzuki, T. Yasui, K. Ishihara, Angew. Chem. 2011, 123, 5443; Angew. Chem. Int. Ed. 2011, 50, 5331.
28. P. A. Levine, A. Walti, Org. Synth. 1943, Coll. Vol. 2, 5.
29. Selected examples:
30. J. D. Cocker, H. B. Henbest, G. H. Phillipps, G. P. Slater, D. A. Thomas, J. Chem. Soc. 1965, 6;
31. M. E. Kuehne, T. C. Giacobbe, J. Org. Chem. 1968, 33, 3359;
32. D. J. Rawilson, G. Sosnovsky, Synthesis 1973, 567;
33. G. J. Williams, N. R. Hunter, Can. J. Chem. 1976, 54, 3830;
34. T. Satoh, S. Motohashi, K. Yamakawa, Bull. Chem. Soc. Jpn. 1986, 59, 946;
35. J. C. Lee, Y. S. Jin, J.-H. Choi, Chem. Commun. 2001, 956; for the stoichiometric use of N-methyl-O-acylhydroxylamines instead of heavy metal salts, see: 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.
36. F. Mizukami, M. Ando, T. Tanaka, J. Imamura, J. Bull. Chem. Soc. Jpn. 1978, 51, 335.
37. R. M. Moriarty, R. K. Vaid, T. E. Hopkins, B. K. Vaid, O. Prakash, Tetrahedron Lett. 1990, 31, 201.
38. Selected reviews:
39. R. M. Moriarty, R. M. Vaid, G. F. Koser, Synlett 1990, 365;
40. R. M. Moriarty, O Prakash in Organic Reactions, Vol. 54, John Wiley & Sons, New York, 1999, p.273;
41. G. F. Koser, Aldrichim. Acta 2001, 34, 89; for recent examples of the organoiodine(III)-mediated oxylactonization of oxocarboxylic acids, see:
42. X. Huang, Q. Zhu, J. Zhang, J. Chem. Res. 2001, 480;
43. R. S. Hou, H.-M. Wang; Y.-C. Lin, L.-C. Chen, Heterocycles 2005, 65, 649.
44. J. Sheng, X. Li, M. Tang, B. Gao, G. Huang, Synthesis 2007, 1165.
45. T. Yamamoto, H. Togo, Synlett 2005, 2486.
46. M. Uyanik, T. Yasui, K. Ishihara, Bioorg. Med. Chem. Lett. 2009, 19, 3848.
47. Selected patents:
48. T. Iwamoto, H. Kitamura, T. Fujimoto (Nitto Kasei), Jpn. Kokai Tokkyo Koho JP2009-144071, 2009;
49. J. Hatakeyama, S. Tachibana, Y. Osawa (Shin-etsu Chemical), Jpn. Kokai Tokkyo Koho JP2009-169406, 2009.
50. S. Yamada, D. Morizono, K. Yamamoto, Tetrahedron Lett. 1992, 33, 4329.
51. D. Griller, K. Ingold, Acc. Chem. Res. 1980, 13, 317;
52. M. Newcomb, C. C. Johnson, M. B. Manek, T. R. Varick, J. Am. Chem. Soc. 1992, 114, 10915.
53. T. Nagano, Z. Jia, X. Li, G. Liu, A. S. C. Chan, T. Hayashi, Chem. Lett. 2010, 39, 929.
54. M. Ngatimin, D. W. Lupton, Aust. J. Chem. 2010, 63, 653.
55. S. M. Altermann, R. D. Richardson, T. K. Page, R. K. Schmidt, E. Holland, U. Mohammed, S. M. Paradine, A. N. French, C. Richter, A. M. Bahar, B. Witulski, T. Wirth, Eur. J. Org. Chem. 2008, 5315.
56. S. Quideau, G. Lyvinec, M. Marguerit, K. Bathany, A. Ozanne-Beaudenon, T. Buffeteau, D. Cavagnat, A. Chenede, Angew. Chem. 2009, 121, 4675; Angew. Chem. Int. Ed. 2009, 48, 4605.
57. T. Dohi, A. Maruyama, N. Takenaga, K. Senami, Y. Minamitsuji, H. Fujioka, S. B. Caemmerer, Y. Kita Angew. Chem. 2008, 120, 3847; Angew. Chem. Int. Ed. 2008, 47, 3787; Angew. Chem. Int. Ed. 2008, 47, 3787.
58. M. Uyanik, T. Yasui, K. Ishihara, Angew. Chem. 2010, 122, 2221; Angew. Chem. Int. Ed. 2010, 49, 2175;
59. M. Uyanik, T. Yasui, K. Ishihara, Tetrahedron 2010, 66, 5841.
60. Recent review: T. D. Sheppard, J. Chem. Res. 2011, 35, 377.
61. Selected examples:
62. Y. Uozumi, K. Kato, T. Hayashi, J. Am. Chem. Soc. 1997, 119, 5063;
63. R. M. Trend, Y. K. Ramtohul, E. M. Ferreira, B. M. Stoltz, Angew. Chem. 2003, 115, 2998; Angew. Chem. Int. Ed. 2003, 42, 2892;
64. S. C. Pelly, S. Govender, M. A. Fernandes, H.-G. Schmalz, C. B. deKoning, J. Org. Chem. 2007, 72, 2857;
65. S. Tanaka, T. Seki, M. Kitamura, Angew. Chem. 2009, 121, 9110; Angew. Chem. Int. Ed. 2009, 48, 8948, and references therein.
66. First report:
67. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 1999, 121, 6519; review:
68. T. Ooi, K. Maruoka, Angew. Chem. 2007, 119, 4300; Angew. Chem. Int. Ed. 2007, 46, 4222.
69. L. Chen, E. Shi, Z. Liu, S. Chen, W. Wei, H. Li, K. Xu, X. Wan, Chem. Eur. J. 2011, 17, 4085.
70. W. Wei, C. Zhang, Y. Xu, X. Wan, Chem. Commun. 2011, 47, 10827.
71. T. Froehr, C. P. Sindlinger, U. Kloeckner, P. Finkbeiner, B. J. Nachtsheim, Org. Lett. 2011, 13, 3754.
72. L. Ma, X. Wang, W. Yu, B. Han, Chem. Commun. 2011, 47, 11333.
73. A. Rodríguez, W. J. Moran, Org. Lett. 2011, 13, 2220.
74. G. Bai, K. Xu, G. Chen, Y. Tang, T. Li, Synthesis 2011, 1599.
75. C. Zhu, Y. Wei, ChemSusChem 2011, 4, 1082.
76. C. Wan, L. Gao, Q. Wang, J. Zhang, Z. Wang, Org. Lett. 2010, 12, 3902;
77. J. Zhang, D. Zhu, C. Yu, C. Wan, Z. Wang, Org. Lett. 2010, 12, 2841;
78. Q. Wang, C. Wan, Y. Gu, J. Zhang, L. Gao, Z. Wang, Green Chem. 2011, 13, 578;
79. Y. Yan, Z. Wang, Chem. Commun. 2011, 47, 9513.