Heck Reactions in Aqueous Miniemulsions
Hazit A. Zayas A , David Valade A , Zhongfan Jia A and Michael J. Monteiro A B
+ Author Affiliations
- Author Affiliations
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 https://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 | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK28Xlt1ygsrs%3D&md5=16aff041732feada5f8467812984bcf6CAS |
[2] M. J. Monteiro, Macromolecules 2010, 43, 1159.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXkt1ahtg%3D%3D&md5=264776ff58183655a9f145044748b127CAS |
[3] R. N. Butler, A. G. Coyne, Chem. Rev. 2010, 110, 6302.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXhtFWlsLvM&md5=eea9a416308fb7d65d6f230fee03a593CAS |
[4] R. F. Heck, Acc. Chem. Res. 1979, 12, 146.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaE1MXhsFWju7g%3D&md5=2f4f9b71ceed16c3d6138b3294b7d477CAS |
[5] K. H. Shaughnessy, R. B. DeVasher, Curr. Org. Chem. 2005, 9, 585.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2MXjs12rtro%3D&md5=74acc433a89b715148da377569bfae0fCAS |
[6] C. Torborg, M. Beller, Adv. Synth. Catal. 2009, 351, 3027.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhs1Sjs77I&md5=fa18f27b608914c2ad304232c6c68026CAS |
[7] A. de Meijere, S. Brase, J. Organomet. Chem. 1999, 576, 88.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK1MXivFOlsr4%3D&md5=e283f7323503491f304ec37d301d9573CAS |
[8] Z. Bao, Y. Chen, R. Cai, L. Yu, Macromolecules 1993, 26, 5281.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DyaK3sXls1Sqsrc%3D&md5=c37d751c8e508d72d0c8bc5410b92545CAS |
[9] B. H. Lipshutz, B. R. Taft, Org. Lett. 2008, 10, 1329.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1cXjtFCqtb8%3D&md5=0551ce47ca5956943842b6a4fc17039bCAS |
[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 | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXlvVSksrY%3D&md5=2f96ff02e5ed0b26cdf980637dff3dafCAS |
[11] M. M. Shinde, S. S. Bhagwat, J. Dispersion Sci. Technol. 2012, 33, 117.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3MXhs1Gru7bE&md5=863ae40ec84d89af36c64ce62771c726CAS |
[12] J. Jiang, C. Cai, J. Dispersion Sci. Technol. 2006, 27, 1137.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XhtFajs7zN&md5=8942290dfda02a520fc5c46f2149a5ddCAS |
[13] Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Org. Lett. 2002, 4, 3371.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD38Xms1Omtbk%3D&md5=c864f9ab6af76fb9b08c2827063ba1d7CAS |
[14] Y. M. A. Yamada, K. Takeda, H. Takahashi, S. Ikegami, Tetrahedron 2004, 60, 4097.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjtVCns7w%3D&md5=cc4ccd14f2a3ea95407aadac383fe905CAS |
[15] J. Jiang, C. Cai, J. Colloid Interface Sci. 2006, 299, 938.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD28XltlSjtLw%3D&md5=5fa50efa92f1ed5732a4053504e3a763CAS |
[16] A. R.-B. Baruch, D. Tsvelikhovsky, M. Schwarze, R. Schomacker, M. Fanun, J. Blum, J. Mol. Catal. Chem. 2010, 323, 65.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXlsFCmu7g%3D&md5=ca99a888124b89db62dd144c6f04ae13CAS |
[17] G. Zhang, H. Zhou, J. Hu, M. Liu, Y. Kuang, Green Chem. 2009, 11, 1428.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXhtVOmtbvN&md5=92601a8c7270f6f679b0cfbb4935ff6bCAS |
[18] D. Tsvelikhovsky, J. Blum, Eur. J. Org. Chem. 2008, 2008, 2417.
| Crossref | GoogleScholarGoogle Scholar |
[19] K. Landfester, Macromol. Rapid Commun. 2001, 22, 896.
| Crossref | GoogleScholarGoogle Scholar |
[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 | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXktl2gt78%3D&md5=248f09b81012ec89a79ae4848eabeae6CAS |
[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.
| 1:CAS:528:DC%2BC38XhvFKlug%3D%3D&md5=0fcef3fccd8d9067833bd0fe6e64c0b9CAS |
[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 | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BC3cXmsVGqt78%3D&md5=0aa90fed651d440d53f69461684cb806CAS |
[24] D. P. C. de Barros, L. P. Fonseca, J. M. S. Cabral, C. K. Weiss, K. Landfester, Biotechnol. J. 2009, 4, 674.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD1MXmvFCgsr4%3D&md5=3b0cc1abfeefc77f315dacada2219028CAS |
[25] E. Hittinger, A. Kokil, C. Weder, Angew. Chem. Int. Edit. 2004, 43, 1808.
| Crossref | GoogleScholarGoogle Scholar | 1:CAS:528:DC%2BD2cXjtV2jtbw%3D&md5=e18371cdcb3af19fc43db677e6c45a58CAS |
