Palladium membrane-installed microchannel devices for instantaneous Suzuki-Miyaura cross-coupling

Chemistry - A European Journal

Volumn 16, Issue 37, 2010, Pages 11311-11319

  Yamada, Yoichi M A ^a   Watanabe, Toshihiro ^a,b   Beppu, Tomohiko ^b   Fukuyama, Naoshi ^b   Torii, Kaoru ^b   Uozumi, Yasuhiro ^a,b  

^a RIKEN   (Japan)

^b GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

Author keywords

Allylic arylation; Membranes; Microreactors; Palladium; Suzuki Miyaura reaction

Indexed keywords

ALKENYL HALIDES; AQUEOUS PHASIS; ARYLATIONS; ARYLBORONIC ACIDS; BIARYLS; BORON REAGENTS; CARBON-CARBON BOND-FORMING REACTIONS; CATALYTIC MEMBRANE; CHANNEL REGION; COMPLEX MEMBRANE; COUPLING PRODUCT; CROSSLINKED; LINEAR POLYMERS; MICRO REACTOR; MICRO-CHANNEL DEVICES; MICRO-FLOW; PALLADIUM MEMBRANE; QUANTITATIVE YIELDS; RESIDENCE TIME; SUZUKI-MIYAURA CROSS-COUPLING; SUZUKI-MIYAURA REACTION;

AROMATIC COMPOUNDS; BORON; BORON COMPOUNDS; CHEMICAL REACTORS; ESTERS; MEMBRANES; MICROCHANNELS; OLEFINS; PALLADIUM; PALLADIUM COMPOUNDS; PHASE INTERFACES; POLYMERS; SODIUM;

CHEMICAL REACTIONS;

EID: 77957191755     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201000511     Document Type: Article

References (75)

1. For a recent review of solid-phase reactions by using palladium catalysts, see: a) Y. Uozumi, T. Hayashi in Handbook of Combinatorial Chemistry (Eds.: K. C. Nicolaou, R. Hanko, W. Hartwig) Wiley-VCH, Weinheim, 2002, Chapter 19
2. T. Franzel, W. Solodenko, A. Kirschning in Polymeric Materials in Organic Synthesis and Catalysis (Ed.: M. R. Buchmeiser), Wiley-VCH, Weinheim, 2003, Chapter 4
3. Y. Uozumi, Top. Curr. Chem. 2004, 242, 77
4. Z. Wang, G. Chen, K. Ding, Chem. Rev. 2009, 109, 322
5. J. Lu, P. H. Toy, Chem. Rev. 2009, 109, 815
6. Y. Uozumi, Y. M. A. Yamada, Chem. Rec. 2009, 9, 51.
7. J.-i. Yoshida, A. Nagaki, T. Yamada, Chem. Eur. J. 2008, 14, 7450-7459
8. C. Wiles, P. Watts, Eur. J. Org. Chem. 2008, 1655
9. J. Kobayashi, Y. Mori, S. Kobayashi, Chem. Asian J. 2006, 1-2,22
10. K. Jahnisch, V. Hessel, H. Lowe, M. Baerns, Angew. Chem. 2004, 116, 410
11. Angew. Chem. Int. Ed. 2004, 43, 406
12. H. Pennemann, V. Hessel, H. Löwe, Chem. Eng. Sci. 2004, 59, 4789
13. P. D. I. Fletcher, S.J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong, X. Zhang, Tetrahedron 2002, 58, 4735
14. S. J. Haswell, R. J. Middleton, B. O'Sullivan, V. Skelton, P. Watts, P. Styring, Chem. Commun. 2001, 391.
15. For recent reports on flow reactors that bear immobilized palladium catalysts for organic synthesis, see: a) G. M. Greenway, S. J. Haswell, D. O. Morgan, V. Skelton, P. String, Sens. Actuators B 2000, 63, 153
16. G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708
17. J. Kobayashi, Y. Mori, K. Okamoto, R. Akiyama, M. Ueno, T. Kitamori, S. Kobayashi, Science 2004, 304, 1305
18. U. Kunz, H. Schönfeld, W. Solodenko, G. Jas, A. Kirschning, Ind. Eng. Chem. Res. 2005, 44, 8458
19. A. Kirschning, W. Solodenko, K. Mennecke, Chem. Eur. J. 2006, 12, 5972
20. I. R. Baxendale, C. M. Griffiths-Jones, S. V. Ley, G. K. Tranmer, Chem. Eur. J. 2006, 12, 4407
21. M. T. Rahman, T. Fukuyama, N. Kamata, M. Sato, I. Ryu, Chem. Commun. 2006, 2236
22. O. Trapp, S. K. Weber, S. Bauch, W. Hofstadt, Angew. Chem. 2007, 119, 7447
23. Angew. Chem. Int. Ed. 2007, 46, 7307
24. T. Fukuyama, M. T. Rahman, M. Sato, I. Ryu, Synlett 2008, 151
25. S. Ceylan, C. Friese, C. Lammel, K. Mazac, A. Kirschning, Angew. Chem. 2008, 120, 9083
26. Angew. Chem. Int. Ed. 2008, 47, 8950
27. M. Ueno, T. Suzuki, T. Naito, H. Oyamada, S. Kobayashi, Chem. Commun. 2008, 1647
28. A. Gomann, J. A. Deverell, K. F. Munting, R. C. Jones, T. Rodemann, A. J. Canty, J. A. Smith, R. M. Guijt, Tetrahedron 2009, 65, 1450.
29. Y. M. A. Yamada, Chem. Pharm. Bull. 2005, 53, 723
30. Y. M. A. Yamada, Y. Uozumi, Org. Lett. 2006, 8, 1375
31. Y. M. A. Yamada, Y. Maeda, Y. Uozumi, Org. Lett. 2006, 8, 4259
32. Y. M. A. Yamada, H. Guo, Y. Uozumi, Org. Lett. 2007, 9, 1501
33. Y. M. A. Yamada, Y. Uozumi, Tetrahedron 2007, 63, 8492
34. Y. M. A. Yamada, Y. Uozumi, Heterocycles 2008, 76, 645.
35. P. J. A. Kenis, R. F. Ismagilov, S. Takayama, G. M. Whitesides, Acc. Chem. Res. 2000, 33, 841
36. P. J. A. Kenis, R. F. Ismagilov, G. M. Whitesides, Science 1999, 285, 83
37. B. Zhao, N. O. L. Viernes, J. S. Moore, D. J. Beebe, J. Am. Chem. Soc. 2002, 124, 5284
38. H. Hisamoto, Y. Shimizu, K. Uchiyama, M. Tokeshi, Y. Kikutani, A. Hibara, T. Kitamori, Anal. Chem. 2003, 75, 350.
39. Y. Uozumi, Y. M. A. Yamada, T. Beppu, N. Fukuyama, M. Ueno, T. Kitamori, J. Am. Chem. Soc. 2006, 128, 15994
40. Y. M. A. Yamada, T. Watanabe, K. Torii, Y. Uozumi, Chem. Commun. 2009, 5594.
41. Purchased from Institute of Microchemical Technology, Co. , Ltd. , (Kanagawa, Japan; http://www.i-mt.co.jp).
42. For a preparation of PA-TAP-Pd for the Suzuki-Miyaura reaction and Mizoroki-Heck reaction, see: a) Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371
43. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, J. Org. Chem. 2003, 68, 7733
44. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Tetrahedron Lett. 2003, 44, 2379
45. Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Tetrahedron 2004, 60, 4087.
46. F. G. Mann, D. Purdie, J. Chem. Soc. 1935, 1549.
47. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457
48. P. He, J. Haswell, P. D. I. Fletcher, Appl. Catal. A 2004, 274, 111
49. N.T.S. Phan, J. Khan, P. Styring, Tetrahedron 2005, 61, 12065.
50. The reaction efficiency was strongly affected by the concentration and the flow rate of each solution of the substrates. Thus, for example, the reaction of 4a (flow rate: 2.5 liLmin-1) and 5a (flow rate: 2.5 μLmin-1) afforded 24% yield of 6 a under otherwise similar conditions.
51. The coupling reaction did not proceed without the catalytic membrane under similar conditions (see section IV in the Supporting Information).
52. Several fractions were collected as random snapshots for each reaction shown in Tables 2-5 to demonstrate the stable and high catalytic performance of the microchannel reactor with a divided catalytic membrane (Figures S3 and S4 in the Supporting Information).
53. I Osaka, R. D. McCullough, Chem. Rev. 2008, 108, 1202
54. U. Mitschke, P. Bäuerle, J. Mater. Chem. 2000, 10, 1471.
55. P. R. Parry, M. R. Bryce, B. Tarbit, Org. Biomol. Chem. 2003, 1, 1447
56. M. S. McClure, B. Glover, E. McSorley, A. Millar, M. H. Osterhout, F. Roschangar, Org. Lett. 2001, 3, 1677.
57. H. Tsukamoto, M. Sato, Y. Kondo, Chem. Commun. 2004, 1200
58. C. Nájera, J. Gil-Moltó, S. Karlström, Adv. Synth. Catal. 2004, 346, 1798
59. K. Manabe, K. Nakada, N. Aoyama, S. Kobayashi, Adv. Synth. Catal. 2005, 347, 1499
60. M. Monreno-Mañas, R. Pleixats, S. Villarroya, Organometallics 2001, 20, 4524
61. G. W. Kabalka, G. Dong, B. Venkataiah, Org. Lett. 2003, 5, 893
62. E. Paetzold, G. Oehme, J. Mol. Catal. A 2000, 152, 69
63. E. Blart, J. P. Genêt, M. Safl, M. Savignac, D. Sinou, Tetrahedron 1994, 50, 505.
64. For palladium-catalyzed arylations of secondary allylic acetates that possess a β-sp2 or-sp3 hydride, see: a) H. Ohmiya, Y. Mikida, T. Tanaka, M. Sawamura, J. Am. Chem. Soc. 2008, 130, 17276
65. G. Ortar, Tetrahedron Lett. 2003, 44, 4311
66. D. Bouyssi, V. Gerusz, G. Balme, Eur. J. Org. Chem. 2002, 2445
67. J.-Y. Legros, J.-C. Flaud, Tetrahedron Lett. 1990, 31, 7453.
68. For a resin-supported Pd-catalyzed arylation of secondary allylic esters that possess a β-sp2 or-sp3 hydride, see: Y. Uozumi, H. Danjo, T. Hayashi, J. Org. Chem. 1999, 64, 3384.
69. D. J. Carini, J. V. Duncia, P. E. Aldrich, A. T. Chiu, A. L. Johnson, M. E. Pierce, W. A. Price, J. B. Santella III, G. J. Wells, J. Med. Chem. 1991, 34, 2525.
70. S. S. Kerwar, Am. J. Med. 1983, 75, 62.
71. G. Lu, R. Franzén, Q. Zhang, Y. Xu, Tetrahedron Lett. 2005, 46, 4255
72. G. A. Grasa, M. S. Viciu, J. Huang, C. Zhang, M. L. Trudell, S. P. Nolan, Organometallics 2002, 21, 2866.
73. N. Tamaoki, T. Yamaoka, J. Chem. Soc. Perkin Trans. 2 1991, 873
74. S. Y. Lee, S. J. Na, H. Y. Kwon, B. Y. Lee, S. O. Kang, Organometallics 2004, 23, 5382
75. R. Sato, G. Hamasaka, T. Yamamoto, H. Muraoka, S. Nakajo, S. Ogawa, Bull. Chem. Soc. Jpn. 2007, 80, 768.