Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations

Journal of Organic Chemistry

Volumn 80, Issue 5, 2015, Pages 2676-2699

  Šturala, Jiří ^a   Boháčová, Soňa ^a   Chudoba, Josef ^a   Metelková, Radka ^a   Cibulka, Radek ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSTS; CATALYTIC OXIDATION; CHEMICAL COMPOUNDS; GIBBS FREE ENERGY; HYDROGEN; HYDROGEN PEROXIDE; PEROXIDES; POSITIVE IONS; SALTS;

CATALYTIC EFFICIENCIES; CHEMO-SELECTIVITY; ELECTRON WITHDRAWING GROUP; ELECTRON-DEFICIENT; ORGANOCATALYTIC; OXIDIZING AGENTS; REDUCTION POTENTIAL; TRIFLUOROMETHYL;

OXIDATION;

HYDROGEN PEROXIDE; HYDROPEROXIDE; NUCLEOPHILE; PYRAZINE DERIVATIVE; PYRIDINIUM DERIVATIVE; PYRIMIDINE DERIVATIVE; SULFOXIDE;

ARTICLE; CATALYSIS; CATALYST; ELECTRON TRANSPORT; OXIDATION; OXYGEN TRANSPORT; OXYGENATION; REACTION ANALYSIS; REDUCTION; SUBSTITUTION REACTION; SULFOXIDATION;

EID: 84924301883     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo502865f     Document Type: Article

References (107)

1. Sheldon, R. A.; Arends, I. W. C. E.; Hanefeld, U. In Green Chemistry and Catalysis; Wiley-VCH: Weinheim, 2007; pp 1-47.
2. Berkessel, A.; Vogl, N. Synthetic Uses of Peroxides. In Chemistry of Peroxides; Rappoport, Z., Ed.; John Wiley & Sons: New York, 2006; Vol. 2, pp 307-596.
3. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 1977
4. Bach, R. D. General and Theoretical Aspects of the Peroxide Group. In Chemistry of Peroxides; Rappoport, Z., Ed.; John Wiley & Sons Ltd.: New York, 2006; Vol. 2, pp 1-92.
5. Modern Oxidation Methods, 2nd Completely Revised; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, 2010.
6. Oxidations. In Transition Metals for Organic Synthesis; Beller, M.; Bolm, C., Ed.; Wiley-VCH: Weinheim, 2008; Part 2, pp 200-507.
7. Caron, S.; Dugger, R. W.; Ruggeri, S. G.; Ragan, J. A.; Ripin, D. H. B. Chem. Rev. 2006, 106, 2943
8. Russo, A.; De Fusco, C.; Lattanzi, A. ChemCatChem 2012, 4, 901
9. Stingl, K. A.; Tsogoeva, S. B. Tetrahedron: Asymmetry 2010, 21, 1055
10. For review on oxidations with heterocyclic hydroperoxides, see: Gelalcha, F. G. Chem. Rev. 2007, 107, 3338
11. Khatmullin, R.; Zhou, D.; Corrigan, T.; Mirzakulova, E.; Glusac, K. D. J. Phys. Org. Chem. 2013, 26, 440
12. Argyrakis, W.; Köppl, C.; Werner, H.-J.; Frey, W.; Baro, A.; Laschat, S. J. Phys. Org. Chem. 2011, 24, 682
13. Makota, O.; Wolf, J.; Trach, Y.; Schulze, B. J. Heterocycl. Chem. 2010, 47, 846
14. Blumenthal, H.; Liebscher, J. ARKIVOC 2009, 204
15. Makota, O.; Eilfeld, A.; Trach, Y.; Schulze, B.; Sieler, J. New J. Chem. 2008, 32, 1020
16. Cibulka, R. Eur. J. Org. Chem. 2015, 915
17. de Gonzalo, G.; Fraaije, M. W. ChemCatChem 2013, 5, 403
18. Imada, Y.; Naota, T. Chem. Rec. 2007, 7, 354
19. Bruice, T. C.; Noar, J. B.; Ball, S. S.; Venkataram, U. V. J. Am. Chem. Soc. 1983, 105, 2452
20. Huijbers, M. M. E.; Montersino, S.; Westphal, A. H.; Tischler, D.; van Berkel, W. J. H. Arch. Biochem. Biophys. 2014, 544, 2
21. Walsh, C. T.; Wencewicz, T. A. Nat. Prod. Rep. 2013, 30, 175
22. Murahashi, S.-I.; Zhang, D.; Iida, H.; Miyawaki, T.; Uenaka, M.; Murano, K.; Meguro, K. Chem. Commun. 2014, 50, 10295
23. Imada, Y.; Ohsaki, M.; Noguchi, M.; Maeda, T.; Fujiki, M.; Kawamorita, S.; Komiya, N.; Naota, T. ChemCatChem 2015, 7, 99
24. Imada, Y.; Kitagawa, T.; Iwata, S.; Komiya, N.; Naota, T. Tetrahedron 2014, 70, 495
25. Ménová, P.; Dvořáková, H.; Eigner, V.; Ludvík, J.; Cibulka, R. Adv. Synth. Catal. 2013, 355, 3451
26. Imada, Y.; Kugimiya, Y.; Iwata, S.; Komiya, N.; Naota, T. Tetrahedron 2013, 69, 8572
27. Imada, Y.; Kitagawa, T.; Wang, H.-K.; Komiya, N.; Naota, T. Tetrahedron Lett. 2013, 54, 621
28. Cibulka, R.; Baxová, L.; Dvořáková, H.; Hampl, F.; Ménová, P.; Mojr, V.; Plancq, B.; Sayin, S. Collect. Czech. Chem. Commun. 2009, 74, 973
29. Imada, Y.; Iida, H.; Ono, S.; Murahashi, S.-I. J. Am. Chem. Soc. 2003, 125, 2868
30. Minidis, A. B. E.; Bäckvall, J.-E. Chem.-Eur. J. 2001, 7, 297
31. Murahashi, S.; Oda, T.; Masui, Y. J. Am. Chem. Soc. 1989, 111, 5002
32. Imada, Y.; Iida, H.; Murahashi, S.-I.; Naota, T. Angew. Chem., Int. Ed. 2005, 44, 1704
33. Mazzini, C.; Lebreton, J.; Furstoss, R. J. Org. Chem. 1996, 61, 8
34. Jurok, R.; Hodačová, J.; Eigner, V.; Dvořáková, H.; Setnička, V.; Cibulka, R. Eur. J. Org. Chem. 2013, 2013, 7724
35. Iida, H.; Iwahana, S.; Mizoguchi, T.; Yashima, E. J. Am. Chem. Soc. 2012, 134, 15103
36. Hartman, T.; Herzig, V.; Buděšínský, M.; Jindřich, J.; Cibulka, R.; Kraus, T. Tetrahedron: Asymmetry 2012, 23, 1571
37. Mojr, V.; Herzig, V.; Buděšínský, M.; Cibulka, R.; Kraus, T. Chem. Commun. 2010, 46, 7599
38. Shinkai, S.; Yamaguchi, T.; Manabe, O.; Toda, F. J. Chem. Soc., Chem. Commun. 1988, 1399
39. Murahashi, S.-I.; Ono, S.; Imada, Y. Angew. Chem., Int. Ed. 2002, 41, 2366
40. Chen, S.; Foss, F. W. Org. Lett. 2012, 14, 5150
41. Kotoučová, H.; Strnadová, I.; Kovandová, M.; Chudoba, J.; Dvořáková, H.; Cibulka, R. Org. Biomol. Chem. 2014, 12, 2137
42. Murray, A. T.; Matton, P.; Fairhurst, N. W. G.; John, M. P.; Carbery, D. R. Org. Lett. 2012, 14, 3656
43. Pouy, M. J.; Milczek, E. M.; Figg, T. M.; Otten, B. M.; Prince, B. M.; Gunnoe, T. B.; Cundari, T. R.; Groves, J. T. J. Am. Chem. Soc. 2012, 134, 12920
44. Bunting, J. W. Tetrahedron 1987, 43, 4277
45. Bunting, J. W.; Bolton, J. L. Tetrahedron 1986, 42, 1007
46. Bunting, J. W.; Fitzgerald, N. P. Can. J. Chem. 1984, 62, 1301
47. Moracci, F. M.; Tortorella, S.; Di Rienzo, B.; Liberatore, F. Tetrahedron 1979, 35, 2591
48. Moracci, F. M.; Liberatore, F.; Tortorella, S.; Di Rienzo, B. Tetrahedron 1979, 35, 809
49. Pitman, I. H.; Sternson, L. A. J. Am. Chem. Soc. 1976, 98, 5234
50. Wallenfels, K.; Hanstein, W. Liebigs Ann. Chem. 1967, 709, 151
51. Ménová, P.; Kafka, F.; Dvořáková, H.; Gunnoo, S.; Šanda, M.; Cibulka, R. Adv. Synth. Catal. 2011, 353, 865
52. Lindén, A. A.; Hermanns, N.; Ott, S.; Krüger, L.; Bäckvall, J.-E. Chem.-Eur. J. 2005, 11, 112
53. Subramanian, L. R.; Martínez, A. G.; Hanack, M.; Surya Prakash, G. K.; Hu, J. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 2001.
54. Friestad, G. K.; Branchaud, B. P. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons: New York, 2001.
55. Kumar, R. Drugs 2008, 68, 1803
56. Ménová, P.; Cibulka, R. J. Mol. Catal. A: Chem. 2012, 363-364, 362
57. Merenyi, G.; Lind, J. J. Am. Chem. Soc. 1991, 113, 3146
58. Ménová, P.; Eigner, V.; Čejka, J.; Dvořáková, H.; Šanda, M.; Cibulka, R. J. Mol. Struct. 2011, 1004, 178
59. Canepa, C.; Bach, R. D.; Dmitrenko, O. J. Org. Chem. 2002, 67, 8653
60. Bach, R. D.; Su, M.-D.; Schlegel, H. B. J. Am. Chem. Soc. 1994, 116, 5379
61. Salt 7 was already prepared by a different procedure; see: Michael Bockman, T.; Kochi, J. K. J. Phys. Org. Chem. 1997, 10, 542
62. Zhou, J.; Li, B.; Qian, Z.-C.; Shi, B.-F. Adv. Synth. Catal. 2014, 356, 1038
63. Taguchi, T.; Yoshihira, K. Chem. Pharm. Bull. 1963, 11, 430
64. Alvarez-Ibarra, C.; Cuervo-Rodriguez, R.; Fernandez-Monreal, M. C.; Ruiz, M. P. J. Org. Chem. 1994, 59, 7284
65. Copenhaver, J. W. Pyrimidines. DE Patent 822086, Nov 1951.
66. Boarland, M. P. V.; McOmie, J. F. W. J. Chem. Soc. (Resumed) 1952, 3716
67. Lian, P.; Wei, H.; Zheng, C.; Nie, Y.; Bian, J.; Bian, Z.; Huang, C. Dalton Trans. 2011, 40, 5476
68. Vanderhaeghe, H.; Claesen, M. Bull. Soc. Chim. Belg. 1957, 66, 276
69. Robba Ann. Chim. 1960, 5, 351
70. Bly, D. D.; Mellon, M. G. J. Org. Chem. 1962, 27, 2945
71. Carr, G. E.; Chambers, R. D.; Holmes, T. F.; Parker, D. G. J. Chem. Soc., Perkin Trans. 1 1988, 921
72. Sperber, N.; Papa, D.; Schwenk, E.; Sherlock, M.; Fricano, R. J. Am. Chem. Soc. 1951, 73, 5752
73. Gohring, W. Process for making pyrimidine derivatives. US Patent 5,883,254, March 1999.
74. Lerner, E. I.; Lippard, S. J. J. Am. Chem. Soc. 1976, 98, 5397
75. Bredereck, H. Organic Syntheses 1963, 5, 794
76. Earl, J. C.; Le Fevre, R. J. W.; Pulford, A. G.; Walsh, A.; Ascher, K. R. S.; Goodman, I.; Davis, M.; Petrow, V.; Bloink, G. J.; Pausacker, K. H.; Felton, D. G. I.; Hull, R. J. Chem. Soc. (Resumed) 1951, 2207
77. Lee, H. W.; Kim, B. Y.; Ahn, J. B.; Kang, S. K.; Lee, J. H.; Shin, J. S.; Ahn, S. K.; Lee, S. J.; Yoon, S. S. Eur. J. Med. Chem. 2005, 40, 862
78. Ugashe, S.; Zheng, W.; Wright, J. J.; Pennell, A. Preparation of pyridinylcarbonylarylsulfonamides as chemokine CCR9 receptor antagonists. Patent WO 2004046092, June 2004.
79. Archer, G. A.; Kalish, R. I.; Ning, R. Y.; Sluboski, B. C.; Stempel, A.; Steppe, T. V.; Sternbach, L. H. J. Med. Chem. 1977, 20, 1312
80. Colla, A.; Martins, M. A. P.; Clar, G.; Krimmer, S.; Fischer, P. Synthesis 1991, 1991, 483
81. Gerus, I. I.; Vdovenko, S. I.; Gorbunova, M. G.; Kukhar, V. P. Chem. Heterocycl. Compd. 1991, 27, 398
82. Plé, N.; Turck, A.; Couture, K.; Quéguiner, G. Synthesis 1996, 1996, 838
83. Okumura, F. S.; Kusaka, H.; Takematsu, T. Bull. Chem. Soc. Jpn. 1960, 33, 1471
84. Whittaker, N.; Jones, T. S. G. J. Chem. Soc. (Resumed) 1951, 1565
85. Wiley, R. H.; Lanet, J.; Hussung, K. H. J. Heterocycl. Chem. 1964, 1, 175
86. van der Plas, H. C.; Jongejan, H.; Koudijs, A. J. Heterocycl. Chem. 1978, 15, 485
87. Speelman, J. C.; Kellogg, R. M. J. Org. Chem. 1990, 55, 647
88. Prostakov, N. S.; Kirillova, L. M.; Klyavina, I. V.; Zakharov, P. I.; Kharlamova, M. D.; Aliev, A. É. Chem. Heterocycl. Compd. 1990, 26, 350
89. Kuthan, J.; Paleček, J. Collect. Czech. Chem. Commun. 1966, 31, 2618
90. Skála, V.; Kuthan, J. Collect. Czech. Chem. Commun. 1970, 35, 2378
91. Winkler, M.; Cakir, B.; Sander, W. J. Am. Chem. Soc. 2004, 126, 6135
92. Pavlov, E. A.; Serazetdinova, V. A.; Kagarlitskii, A. D.; Suvorov, B. V. Chem. Heterocycl. Compd. 1971, 4, 488
93. Gorbyleva, O. I.; Evstratova, M. I.; Yakhontov, L. N. Chem. Heterocycl. Compd. 1983, 19, 1133
94. Evstratova, M. I.; Prokopov, A. A.; Ivanova, I. L.; Markova, I. G.; Tubina, I. S.; Anisimova, O. S.; Skwirskaya, N. V.; Kan, I. I.; Suvorov, B. V.; Yakhontov, L. N. Pharm. Chem. J. 1985, 19, 126
95. Zhang, H.; Chen, C.; Liu, R. Synth. Commun. 2011, 42, 811
96. Bicherov, A. V.; Akopova, A. R.; Spiglazov, V. I.; Morkovnik, A. S. Russ. Chem. Bull. 2010, 59, 91
97. Ali, M. H.; Kriedelbaugh, D.; Wencewicz, T. Synthesis 2007, 2007, 3507
98. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011
99. Hendriks, C. M. M.; Lamers, P.; Engel, J.; Bolm, C. Adv. Synth. Catal. 2013, 355, 3363
100. Rioz-Martínez, A.; de Gonzalo, G.; Pazmiño, D. E. T.; Fraaije, M. W.; Gotor, V. Eur. J. Org. Chem. 2010, 2010, 6409
101. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc., Wallingford, CT, 2013.
102. Becke, A. D. J. Chem. Phys. 1993, 98, 5648
103. Boese, A. D.; Martin, J. M. L. J. Chem. Phys. 2004, 121, 3405
104. Peverati, R.; Truhlar, D. G. Phys. Chem. Chem. Phys. 2012, 14, 16187
105. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158
106. Zhao, Y.; Truhlar, D. G. Theor. Chem. Acc. 2008, 120, 215
107. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669