Instantaneous carbon-carbon bond formation using a microchannel reactor with a catalytic membrane

Journal of the American Chemical Society

Volumn 128, Issue 50, 2006, Pages 15994-15995

  Uozumi, Yasuhiro ^a   Yamada, Yoichi M A ^a   Beppu, Tomohiko ^a   Fukuyama, Naoshi ^a   Ueno, Masaharu ^b   Kitamori, Takehiko ^b  

^a GRADUATE UNIVERSITY FOR ADVANCED STUDIES   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; MEMBRANE; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; REACTION ANALYSIS; REACTOR; SUZUKI REACTION;

EID: 33845593714     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja066697r     Document Type: Article

References (22)

1. Haswell, S. J.; Middleton, R. J.; O'Sullivan, B.; Skelton, V.; Watts, P.; Styring, P. Chem. Commun. 2001, 391.
2. Fletcher, P. D. I.; Haswell, S. J.; Pombo-Villar, E.; Warrington, B. H.; Watts, P.; Wong, S. Y. F.; Zhang, X. Tetrahedron 2002, 58, 4735.
3. Pennemann, H.; Hessel, V.; Löwe, H. Chem. Eng. Sci. 2004, 59, 4789.
4. For recent reports on flow-reactors bearing immobilized palladium catalysts, see: (a) Jas, G.; Kirschning, A. Chem.-Eur. J. 2003, 9, 5708.
5. (b) Kirschning, A.; Solodenko, W.; Mennecke, K. Chem.-Eur. J. 2006, 12, 5972.
6. (c) Kunz, U.; Schönfeld, H.; Solodenko, W.; Jas, G.; Kirschning, A. Ind. Eng. Chem. Res. 2005, 44, 8458.
7. (d) Baxendale, I. R.; Griffiths-Jones, C. M.; Ley, S. V.; Tranmer, G. K. Chem.-Eur. J. 2006, 12, 4407.
8. Kobayashi, J.; Mori, Y.; Kobayashi, S. Chem. Asian J. 2006, 1-2, 22.
9. Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.; Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305.
10. (a) Kenis, P. J. A.; Ismagilov, R. F.; Whitesides, G. M. Science 1999, 285, 83.
11. (b) Zhao, B.; Viernes, N. O. L.; Moore, J. S.; Beebe, D. J. J. Am. Chem. Soc. 2002, 124, 5284.
12. (c) Hisamoto, H.; Shimizu, Y.; Uchiyama, K.; Tokeshi, M.; Kikutani, Y.; Hibara, A.; Kitamori, T. Anal. Chem. 2003, 75, 350.
13. Yamada, Y. M. A.; Takeda, K.; Takahashi, H.; Ikegami, S. Org. Lett. 2002, 4, 3711.
14. Purchased from Institute of Microchemical Technology, Co., Ltd., Kanagawa, Japan: URL: http://www.i-mt.co.jp.
15. 3, palladium loading = 0.37 mmol/g (3.2 μmol/channel).
16. (a) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
17. (b) He, P.; Haswell, J.; Fletcher, P. D. I. Appl. Catal., A 2004, 274, 111.
18. (c) Phan, N. T. S.; Khan, J.; Styring, P. Tetrahedron 2005, 61, 12065.
19. The coupling reaction did not proceed without the catalytic membrane under similar conditions.
20. Several fractions were collected as random snapshots for each reaction shown in Table 1 to demonstrate the stable and high catalytic performance of the microchannel reactor with a divided catalytic membrane.
21. Takizawa, S.; Somei, H.; Jayaprakash, D.; Sasai, H. Angew. Chem., Int. Ed. 2003, 42, 5711.
22. Wang, X.; Ding, K. J. Am. Chem. Soc. 2004, 126, 10524.