Oxidations of allylic and benzylic alcohols under inductively-heated flow conditions with gold-doped superparamagnetic nanostructured particles as catalyst and oxygen as oxidant

IUBMB Life

Volumn 356, Issue 17, 2014, Pages 3530-3538

  Chaudhuri, Sangeeta Roy ^a   Hartwig, Jan ^a   Kupracz, Lukas ^a   Kodanek, Torben ^a   Wegner, Jens ^a   Kirschning, Andreas ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

Author keywords

Flow chemistry; Gold; Inductive heating; Nanostructures; Oxidation; Superparamagnetism

Indexed keywords

ALCOHOL DERIVATIVE; ALLYL COMPOUND; ALLYLIC ALCOHOL DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; GOLD NANOPARTICLE; OXYGEN; SILICON DIOXIDE; SUPERPARAMAGNETIC IRON OXIDE NANOPARTICLE; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CATALYST; CONTROLLED STUDY; ELECTROMAGNETIC FIELD; FLOW; FLOW RATE; HEAT TRANSFER; HEATING; MASS SPECTROMETRY; PARTICLE SIZE; SURFACE PROPERTY;

EID: 84915750980     PISSN: 15216543     EISSN: 15216551     Source Type: Journal    
DOI: 10.1002/adsc.201400261     Document Type: Article

References (110)

1. S. V. Ley, A. Madin, B. M. Trost, I. Fleming, in: Comprehensive Organic Synthesis, Vol 7, Pergamon Press, Oxford, 1991, pp 305-327
2. b) R. C Larock, Comprehensive Organic Transformations, VCH Publishers, New York, 1989, 604 pp.
3. S. V. Ley,A. Madin,B. M. Trost,I. Flemming in: Comprehensive Organic Synthesis Vol 7 Pergamon Press, Oxford 1991 251-289.
4. V. V. Zhdankin, J. Org. Chem. 2011, 76, 1185-1197.
5. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
6. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071.
7. R. V. Stevens, K. T. Chapman, H. N. Weller, J. Org. Chem. 1980, 45, 2030-2032.
8. P.-L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562
9. b) M. Lei, R.-J. Hu, Y.-G. Wang, Tetrahedron 2006, 62, 8928-8932
10. c) M. Shibuya, M. Tomizawa, Y. Iwabuchi, Org. Lett. 2008, 10, 4715-4718.
11. A.-K. C. Schmidt, C. B. W. Stark, Org. Lett. 2011, 13, 4164-4167.
12. A. Kirschning, C. Altwicker, G. Dr-ger, J. Harders, N. Hoffmann, U. Hoffmann, H. Schçnfeld, W. Solodenko, U. Kunz, Angew. Chem. 2001, 113, 4118-4120
13. Angew. Chem. Int. Ed. 2001, 40, 3995-3998
14. b) N. Amberdeen, R. Kumar, T. Wirth, Beilstein J. Org. Chem. 2013, 9, 1437-1442
15. c) J. F. Greene, J. M. Hoover, D. S. Mannel, T. W. Root, S. S. Stahl, Org. Process Res. Dev. 2013, 17, 1247-1251.
16. R. Chorghade, Cl. Battilocchio, J. M. Hawkins, S. V. Ley, Org. Lett. 2013, 15, 5698-5701.
17. Reviews: a) M. Besson, P. Gallezot, Catal. Today 2000, 57, 127-141
18. b) R. A. Sheldon, I.W. C. E. Arends, G.-J. ten Brink, A. Dijksman, Acc. Chem. Res. 2002, 35, 774-781
19. c) T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058
20. d) B.-Z. Zhan, A. Thompson, Tetrahedron 2004, 60, 2917-2935
21. M. J. Schultz, M. S. Sigman, Tetrahedron 2006, 62, 8227-8241
22. f) T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J. 2008, 3, 196-214
23. g) C. Parmeggianni, F. Cardona, Green Chem. 2012, 14, 547-564.
24. N. Zotova, K. Hellgardt, G. H. Helsall, A. S. Jessiman, K. K. M. Hii, Green Chem. 2010, 12, 2147-2163.
25. T. Nakano, Y. Ishii, M. Ogawa, J. Org. Chem. 1987, 52, 4855-4859
26. b) K. Kaneda, M. Fujii, K. Morioka, J. Org. Chem. 1996, 61, 4502-4503
27. S. Ya mazaki Chem. Lett. 1989 18 1361-1364
28. d) A. F. Lee, J. J. Gee, H. J. Theyers, Green Chem. 2000, 2, 279-282
29. e) Y. Kon, Y. Usui, K. Sato, Chem. Commun. 2007, 4399-4400
30. f) J. Liu, F. Wang, R. Dewil, Catal. Lett. 2009, 130, 448-454
31. g) L. Tonucci, M. Nicastro, N. d 'Alessandro, M. Bressan, P. D'Ambrosio, A. Morvillo, Green Chem. 2009, 11, 816-820.
32. G. C. Bond, P. A. Sermon, G. Webb, D. A. Buchanan, P. B. Wells, J. Chem. Soc. Chem.Commun. 1973, 444-445
33. b) G. J. Hutchings, J. Catal. 1985, 96, 292-295
34. c) M. Haruta, T. Kobayashi, H. Sano, N. Yamada, Chem. Lett. 1987, 16, 405-408
35. d) J.-D. Grunwal dt, C. Kiener, C. Wçgerbauer, A. Baiker, J. Catal. 1999, 181, 223-232.
36. T. Amaya, T. Ito, T. Hirao, Tetrahedron Lett. 2013, 54, 2409-2411
37. b) J. Mielb y, S. Kegnaes, P. Fristrup, ChemCatChem 2012, 4, 1037-1047
38. c) C. D. Pina, E. Falletta, M. Rossi, Chem. Soc. Rev. 2012, 41, 350-369
39. d) A. Corma, H. Garcia, Che m. Soc. Rev. 2008, 37, 2096-2126
40. e) L. Aschwanden, T. Mallet, M. Maciejewski, F. Krumeich, A. Baiker, ChemCatChem 2010, 2, 666-673.
41. A. Abad, A. Corma, H. Garcia, Chem. Eur. J. 2008, 14, 212-222
42. b) C. Almela, A. Corma, H. Garcia, Chem. Commun. 2006, 3178-3180
43. c) C. Della Pina, E. Falleta, L. Patri, M. Rossi, Chem. Soc. Rev. 2008, 37, 2077-2095.
44. M. Chen, W. Goodman, Chem. Soc. Rev. 2008, 37, 1860-1870.
45. N. Lopez, T. V. W. Janssens, B. S. Clausen, Y. Xu, M. Mavrikakis, T. Bligaard, J. K. Nørskov, J. Catal. 2004, 223, 232-235.
46. A. Sanchez, S. Abbet, U. Heiz, W. D. Schneider, H. H-kkinen, R. N. Barnett, U. Landman, J. Phys. Chem. A 1999, 103, 9573-9578
47. b) M. Mavrikakis, P. Stoltze, J. K. Nørskov, Catal. Lett. 2000, 64, 101-106.
48. L. M. Rossi, I. M. Nangoi, N. J. S. Costa, Inorg. Chem. 2009, 48, 4640-4642
49. b) M. J. Jacinto, P. K. Kiyohara, S. H. Masunaga, R. F. Jardim, L. M. Rossi, Appl. Catal. A 2008, 338, 52-57
50. c) M. Kotani, T. Koibe, K. Yamaguchi, N. Mizuno, Green Chem. 2006, 8, 735-741
51. d) A. Hu, G. T. Yee, W. Lin, J. Am. Chem. Soc. 2005, 127, 12486-12487.
52. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058
53. b) R. L. Oliveira, D. Zanchet, P. K. Kiyohara, L. M. Rossi, Chem. Eur. J. 2011, 17, 4626-4631.
54. A. Kirschning, W. Solodenko, K. Mennecke, Chem. Eur. J. 2006, 12, 5972-5990.
55. A. Kirschning, L. Kupracz, J. Hartwig, Chem. Lett. 2012, 41, 562-570
56. b) J. Wegner, S. Ceylan, A. Kirschning, Adv. Synth. Catal. 2012, 354, 17-57
57. c) A.-H. Lu, E. L. Salabas, F. Sch-th, Angew. Chem. 2007, 119, 1242-1266
58. Angew. Chem. Int. Ed. 2007, 46, 1222-1244.
59. Selected reviews a) V. Hessel, A. Renken, J. C. Schouten, J. Yoshida, (Eds. , Micro Process Engineering Wiley-Blackwell, Oxford 2009
60. b) T. Wirth, (Ed.), Microreactors in Organic Synthesis, Wiley-VCH, Weinheim, 2008
61. c) P. B. Mason, K. E. Price, J. L. Steinbacher, A. R. Bogdan, D. T. McQuade, Chem. Rev. 2007, 107, 2300-2318
62. d) D. Webb, T. F. Jamison, Chem. Sci. 2010, 1, 675-680
63. e) J. Yoshida, A. N agaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450-7459.
64. P. B. Palde, T. F. Jamison, Angew. Chem. 2011, 123, 3587-3590
65. Angew. Chem. Int. Ed. 2011, 50, 3525-3528
66. b) B. Gutmann, J.-P. Roduit, D. Roberge, C. O. Kappe, Angew. Chem. 2010, 122, 7255-7259
67. Angew. Chem. Int. Ed. 2010, 49, 7101-7105.
68. J. Wegner, A. Ceylan, C. Friese, A. Kirschning, Eur. J. Org. Chem. 2010, 4372-4375
69. J. Sedelmeier,S. V. Ley,I. R. Baxendale,M. Baumann Org. Lett. 2010, 12, 3618-3621
70. b) J. Sedelmeier, S. V. Ley, I. R. Baxendale, M. Baumann, Org. Lett. 2010, 12, 3618-3621 c) M. O-Brien, I. R. Baxendale, S. V. Ley, Org. Lett. 2010, 12, 1596-1598
71. d) T. Kawaguchi, H. Miyata, K. Ataka, K. Mae, J. Yoshida, Angew. Chem. 2005, 117, 2465-2468
72. Angew. Chem. Int. Ed. 2005, 44, 2413-2416
73. e) M. A. Subhani, M. Bei gi, P. Eilbracht, Adv. Synth. Catal. 2008, 350, 2903-2909
74. f) A. Bogdan, D. T. McQuade, Beilstein J. Org. Chem. 2009, 5, 1-7
75. g) A. B. Leduc, T. F. Jamison, Org. Process Res. Dev. 2012, 16, 1082-1089
76. h) S. Kobayashi, H. Miyamura, R. Akiyama, T. Ishida, J. Am. Chem. Soc. 2005, 127, 9251-9254
77. i) N. Zotova, K. Hellgradt, G. H. Kelsall, A. S. Jessiman, K. K. Hii, Green Chem. 2010, 12, 2157-2163.
78. S. Ceylan, C. Friese, C. Lammel, K. Mazac, A. Kirschning, Angew. Chem. 2008, 120, 9083-9086
79. Angew. Chem. Int. Ed. 2008, 47, 8950-8953
80. b) J. Wegner, S. Ceylan, C. Friese, A. Kirschning, Eur. J. Org. Chem. 2010, 4372-4375
81. c) S. Ceylan, L. Coutable, J. Weg ner, A. Kirschning, Chem. Eur. J. 2011, 17, 1884-1893
82. d) L. Kupracz, J. Hartwig, J. Wegner, S. Ceylan, A. Kirschning, Beilstein J. Org. Chem. 2011, 7, 1441-1448
83. e) S. Cludius-Brandt, L. Kupracz, A. Kirschning, Beilstein J. Org. Chem. 2013, 9, 1745-1750.
84. J. Hartwig, S. Ceylan, L. Kupracz, L. Coutable, A. Kirschning, Angew. Chem. 2013, 125, 9995-9999
85. Angew. Chem. Int. Ed. 2013, 52, 9813-9817
86. b) L. Kupracz, A. Kirschning, Adv. Synth. Catal. 2013, 355, 3369-3374.
87. G. C. Bond, D. T. Thompson, Catal. Rev. Sci. Eng. 1999, 41, 319-388.
88. N. Zheng, G. D. Stucky, J. Am. Chem. Soc. 2006, 128, 14278-14280.
89. MAGSILICA-was obtained from EVONIK Industries AG, Essen, Germany.
90. MAGSILICA-1 was first refluxed in water for 2 h and then dried under vacuum for 16 h for achieving the clustering that is required when it is utilized as reactor fixed bed material.
91. M. Haruta, Cattech 2002, 6, 102-115
92. b) J. L. Townson, Y.-S. L in, J. O. Agola, E. C. Carnes, H. S. Leong, J. D. Lewis, C. L. Haynes, J. Am. Chem. Soc. 2013, 135, 16030-16033.
93. A. Gunther, K. F. Jensen, Lab Chip 2006, 6, 1487-1503.
94. V. Hessel, P. Angeli, A. Gavriilidis, H. Lçwe, Ind. Eng. Chem. Res. 2005, 44, 9750-9769
95. b) S. Kuhn, K. F. Jensen, Ind. Eng. Chem. Res. 2012, 51, 8999-9006
96. c) Y. Wada, M. A. Schmidt, K. F. Jensen, Ind. Eng. Chem. Res. 2006, 45, 8036-8042
97. d) K. K. Yeong, A. Gavriilidis, R. Zapf, V. Hessel, Chem. Eng. Sci. 2004, 59, 3491-3494.
98. S. L. Bourne, P. Koos, M. O-Brien, B. Martin, B. Schenkel, I. R. Baxendale, S. V. Ley, Synlett 2011, 2643-2647
99. b) S. Kasinathan, S. L. Bourne, P. Tolstoy, P. Koos, M. O-Brien, R. W. Bates, I. R. Baxendale, S. V. Ley, Synlett 2011, 2648-2651
100. c) P. Koos, U. Gross, A. Polyzos, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2011, 9, 6903-6908
101. d) M. O-Brien, N. Taylor, A. Polyzos, I. R. Baxendale, S. V. Ley, Chem. Sci. 2011, 2, 1250-1257
102. e) A. Poly zos, M. O-Brien, T. P. Petersen, I. R. Baxendale, S. V. Ley, Angew. Chem. 2011, 123, 1222-1225
103. Angew. Chem. Int. Ed. 2011, 50, 1190-1193
104. f) D. L. Browne, M. O-Brien, P. Koos, P. B. Cranwell, A. Polyzos, S. V. Ley, Synlett 2012, 1402-1406
105. g) P. B. Cranwell, M. O-Brien, D. L. Browne, P. Koos, A. Polyzos, M. Pena-Lopez, S. V. Ley, Org. Biomol. Chem. 2012, 10, 5774-5779
106. h) T. P. Petersen, A. Polyzos, M. O-Brien, T. Ulven, I. R. Baxendale, S. V. Ley, ChemSusChem 2012, 5, 274-277.
107. I. Pinnau, L. G. Toy, J. Membr. Sci. 1996, 109, 125-133.
108. See also: R. L. Oliveria, P. K. Kiyohara, L. M. Rossi, Green Chem. 2010, 12, 144-149.
109. Worthy of note is that pyridine-3-ylmethanol (300 mg) was pumped through the PEEK reactor to yield 280 mg of crude nicotine aldehyde 5h after 12 h of continuous operation without loss of activity of the catalytic system.
110. Nanoparticle architectures based on silica coated iron oxide and gold have also been considered as potential drug delivery systems: B. Wu, S. Tang, M. Chen, N. Zheng, Chem. Commun. 2014, 50, 174-176.