|
Heck Reactions in Aqueous Miniemulsions
Hazit A.
Zayas
A
,
David
Valade
A
,
Zhongfan
Jia
A
and
Michael J.
Monteiro
A
B
A
Australian Institute for Bioengineering and Nanotechnology, University of Queensland, Brisbane, Qld 4072, Australia. B
Corresponding author. Email: m.monteiro@uq.edu.au
Australian Journal of Chemistry
65(8)
1090-1094 http://dx.doi.org/10.1071/CH12164
Submitted: 22 March 2012 Accepted: 24 April 2012 Published:
30
May
2012
|  |
|
|
Abstract
Carrying out organic reactions in water-based nanoreactors represents a ‘green’ method for the preparation of organic compounds. This process eliminates the need for solvents, thus reducing the effect of high volumes of solvent on the environment. In this work, we demonstrate a successful Heck cross-coupling reaction, one of the most used approaches to form C–C bonds using a palladium catalyst, in a miniemulsion. The miniemulsion droplet sizes were small (25 to 42 nm), and the reactions resulted in high conversions of three different products with high trans stereoisomers. 
|
References
[1]
S. Tascioglu, Tetrahedron 1996, 52, 11113.
| CrossRef | CAS |
[2]
M. J. Monteiro, Macromolecules 2010, 43, 1159.
| CrossRef | CAS |
[3]
R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110, 6302.
| CrossRef | CAS |
[4]
R. F. Heck, Acc. Chem. Res. 1979, 12, 146.
| CrossRef | CAS |
[5]
K. H. Shaughnessy, R. B. DeVasher, Curr. Org. Chem. 2005, 9, 585.
| CrossRef | CAS |
[6]
C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027.
| CrossRef | CAS |
[7]
A. de Meijere, S. Brase, J. Organomet. Chem. 1999, 576, 88.
| CrossRef | CAS |
[8]
Z. Bao, Y. Chen, R. Cai, L. Yu, Macromolecules 1993, 26, 5281.
| CrossRef | CAS |
[9]
B. H. Lipshutz, B. R. Taft, Org. Lett. 2008, 10, 1329.
| CrossRef | CAS |
[10]
B. H. Lipshutz, S. Ghorai, A. R. Abela, R. Moser, T. Nishikata, C. Duplais, A. Krasovskiy, R. D. Gaston, R. C. Gadwood, J. Org. Chem. 2011, 76, 4379.
| CrossRef | CAS |
[11]
M. M. Shinde, S. S. Bhagwat, J. Dispersion Sci. Technol. 2012, 33, 117.
| CrossRef | CAS |
[12]
J. Jiang, C. Cai, J. Dispersion Sci. Technol. 2006, 27, 1137.
| CrossRef | CAS |
[13]
Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371.
| CrossRef | CAS |
[14]
Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Tetrahedron 2004, 60, 4097.
| CrossRef | CAS |
[15]
J. Jiang, C. Cai, J. Colloid Interface Sci. 2006, 299, 938.
| CrossRef | CAS |
[16]
A. R.-B. Baruch, D. Tsvelikhovsky, M. Schwarze, R. Schomacker, M. Fanun, J. Blum, J. Mol. Catal. Chem. 2010, 323, 65.
| CrossRef | CAS |
[17]
G. Zhang, H. Zhou, J. Hu, M. Liu, Y. Kuang, Green Chem. 2009, 11, 1428.
| CrossRef | CAS |
[18]
D. Tsvelikhovsky, J. Blum, Eur. J. Org. Chem. 2008, 2008, 2417.
| CrossRef |
[19]
K. Landfester, Macromol. Rapid Commun. 2001, 22, 896.
| CrossRef |
[20]
F. J. Schork, Y. Luo, W. Smulders, J. P. Russum, A. Butté, K. Fontenot, in Miniemulsion Polymerization Polymer Particles 2005, p. 129 (Ed. M. Okubo) (Springer: Berlin).
[21]
E. Schreiber, U. Ziener, A. Manzke, A. Plettl, P. Ziemann, K. Landfester, Chem. Mater. 2009, 21, 1750.
| CrossRef | CAS |
[22]
P. Dolcet, M. Casarin, C. Maccato, L. Bovo, G. Ischia, S. Gialanella, F. Mancin, E. Tondello, S. Gross, J. Mater. Chem. 2012, 22, 1620.
| CAS |
[23]
D. P. C. de Barros, L. P. Fonseca, J. M. S. Cabral, E. M. Aschenbrenner, C. K. Weiss, K. Landfester, Biotechnol. Bioeng. 2010, 106, 507.
| CrossRef | CAS |
[24]
D. P. C. de Barros, L. P. Fonseca, J. M. S. Cabral, C. K. Weiss, K. Landfester, Biotechnol. J. 2009, 4, 674.
| CrossRef | CAS |
[25]
E. Hittinger, A. Kokil, C. Weder, Angew. Chem. Int. Edit. 2004, 43, 1808.
| CrossRef | CAS |
|
|
 |
Subscriber Login |
 |
|