CSIRO Publishing blank image blank image blank image blank imageBooksblank image blank image blank image blank imageJournalsblank image blank image blank image blank imageAbout Usblank image blank image blank image blank imageShopping Cartblank image blank image blank image You are here: Journals > Australian Journal of Chemistry   
Australian Journal of Chemistry
Journal Banner
  An international journal for chemical science
 
blank image Search
 
blank image blank image
blank image
 
  Advanced Search
   

Journal Home
About the Journal
Editorial Board
Contacts
For Advertisers
Content
Online Early
Current Issue
Just Accepted
All Issues
Virtual Issues
Special Issues
Research Fronts
Sample Issue
Covers
For Authors
General Information
Notice to Authors
Submit Article
Open Access
For Referees
Referee Guidelines
Review Article
For Subscribers
Subscription Prices
Customer Service
Print Publication Dates

blue arrow e-Alerts
blank image
Subscribe to our Email Alert or RSS feeds for the latest journal papers.

red arrow Connect with us
blank image
facebook twitter youtube

Affiliated with RACI

Royal Australian Chemical Institute
Royal Australian
Chemical Institute


 

Article << Previous     |     Next >>   Contents Vol 66(4)

Aqueous Microemulsions as Efficient and Versatile Media for Transition-Metal-Catalyzed Reactions

Jason G. Taylor A and Jailton Ferrari B C

A Departamento de Química, ICEB, Universidade Federal de Ouro Preto, UFOP, Campus Universitário Morro do Cruzeiro, 35400-000, Ouro Preto-MG, Brazil.
B Departamento de Química, CCEN, Universidade Federal da Paraíba, UFPB, Campus I, João Pessoa, Paraíba, CEP 58051-970, Brazil.
C Corresponding author. Email: jferrari@quimica.ufpb.br

Australian Journal of Chemistry 66(4) 470-476 http://dx.doi.org/10.1071/CH12492
Submitted: 1 November 2012  Accepted: 18 December 2012   Published: 31 January 2013


 
PDF (1.8 MB) $25
 Export Citation
 Print
  
Abstract

The search for efficient and versatile reaction medium to perform transition-metal-catalyzed reactions is a continuous challenge to the synthetic community. Organic solvents have been traditionally employed for this task, nevertheless, new environmentally friendly, safe, and economically viable alternatives are still highly sought after. In this context, herein, we present an overview of some interesting applications of aqueous microemulsions (oil-in-water, O/W) for transition metal catalyzed reactions as an alternative and promising aqueous-organic reaction medium that has been found to be a highly effective tool in overcoming some environmental or practical issues presented by traditional organic solvents.





References

[1]     (a) For selected general references on transition-metal-catalyzed C–C bond-forming reactions, see:Metal-Catalyzed Cross-Coupling Reaction (Eds A. de Meijere, F. Diederich) 2004, 2nd edn, Vols 1 and 2 (Wiley-VCH: Weinheim).
         (b) Transition Metals for Organic Synthesis (Eds M. Bellar, C. Bolm) 2004, 2nd edn (Wiley-VCH: Weinheim).
         (c) M. Beller, A. Zapf, in Handbook of Organopalladium Chemistry for Organic Synthesis (Eds E.-i. Negishi, A. de Meijeire) 2002, Vol. 1, pp. 1209–1222 (Wiley: New York, NY).

[2]  (a) For selected reviews on transition-metal-catalyzed C­–heteroatom bond-forming reactions, see: S. V. Ley, A. W. Thomas, Angew. Chem. Int. Ed. 2003, 42, 5400.
         | CAS |
      (b) P. Espinet, A. Echavarren, Angew. Chem. Int. Ed. 2004, 43, 4704.

[3]  (a) For selected examples on transition-metal-catalyzed reactions performed in traditional organic solvents, see: Z. Zhou, Y. Xie, Z. Du, Q. Hu, J. Xue, J. Shi, ARKIVOC 2012, vi, 164.
      (b) H.-J. Xu, Y.-Q. Zhao, X.-F. Zhou, J. Org. Chem. 2011, 76, 8036.
         | CrossRef |
      (c) A. Komáromi, F. Szabó, Z. Novák, Tetrahedron Lett. 2010, 51, 5411.
         | CrossRef |

[4]  (a) For a review on organic reactions performed in aqueous media, see: A. Chanda, V. Fokin, Chem. Rev. 2009, 109, 725.
         | CrossRef | CAS |
      (b) V. Polshettiwar, A. Decottignies, C. Len, A. Fihri, ChemSusChem 2010, 3, 502.
         | CrossRef |

[5]  J. H. Fendler, E. J. Fendler, Catalysis in Micellar and Macromolecular Systems 1975 (Academic Press: New York, NY).

[6]  M. Malmsten, Surfactants and Polymers in Drug Delivery 2002 (Marcel Dekker: New York, NY).

[7]  Dynamics of Surfactant Self-Assemblies: Micelles, Microemulsions, Vesicles, and Lyotropic Phases (Ed. R. Zana) 2005 (Taylor & Francis: Boca Raton, FL).

[8]  (a) For some examples on surfactants for metal-catalyzed cross-couplings see: B. H. Lipshutz, S. Ghorai, A. R. Abela, R. Moser, T. Nishikata, C. Duplais, A. Krasovskiy, J. Org. Chem. 2011, 76, 4379.
         | CrossRef | CAS |
      (b) B. H. Lipshutz, S. Ghorai, Aldrichim Acta 2008, 41, 59.

[9]     (a) Microemulsions: Background, New Concepts, Applications, Perspectives (Ed. C. Stubenrauch) 2009 (John Wiley & Sons, Ltd: Chichester).
         (b) M. Bourrel, R. S. Schechter, Microemulsions and Related Systems: Formulation, Solvency and Physical Properties 1988 (Marcel Dekker: New York, NY).

[10]  P. Eychenne, E. Perez, I. Rico, M. Bom, A. Lattes, A. Moisand, Colloid Polym. Sci. 1993, 271, 1049.
         | CrossRef | CAS |

[11]  M. Gautier, L. Rico, A. Lattes, J. Org. Chem. 1990, 55, 1500.
         | CrossRef | CAS |

[12]  B. A. Burnside, L. L. Szafraniec, B. L. Knier, H. D. Durst, R. A. Mackay, F. R. Longo, J. Org. Chem. 1988, 53, 2009.
         | CrossRef | CAS |

[13]  (a) N. Alandis, I. Rico, A. Lattes, Bull. Soc. Chim. Fr. 1989, 2, 252.
      (b) P. Blach, Z. Böstrom, S. Franceschi-Messant, A. Lattes, E. Perez, I. Rico-Lattes, Tetrahedron 2010, 66, 7124.
         | CrossRef |

[14]  M. Häger, F. Currie, K. Holmberg, Colloid Surface A 2004, 250, 163.
         | CrossRef |

[15]  A. Lattes, A. De Savignac, A. Ahmad-Zadeh Samii, Tetrahedron 1987, 43, 1725.
         | CrossRef | CAS |

[16]  (a) For selected examples see A. Lattes, I. Rico, Colloid Surface 1989, 35, 221.
         | CrossRef | CAS |
      (b) Z. Saïdi, C. Boned, J. Peyrelasse, Prog. Colloid Polym. Sci. 1992, 89, 156.
         | CrossRef |

[17]  J. Zhang, B. Han, J. Li, Y. Zhao, G. Yang, Angew. Chem. Int. Ed. 2011, 50, 9911.
         | CrossRef | CAS |

[18]  M. Kahlweit, R. Strey, G. Busse, J. Phys. Chem. 1990, 94, 3881.
         | CrossRef | CAS |

[19]  C. Manoharan, A. Basarkar, J. Singh, in Pharmaceutical Suspensions: From Formulation Development to Manufacturing (Eds A. K. Kulshreshtha, O. N. Singh, G. M. Wall) 2010, pp. 1–37 (Springer: New York, NY).

[20]  R. Nagarajan, E. Ruckenstein, Langmuir 2000, 16, 6400.
         | CrossRef | CAS |

[21]  (a) P. A. Winsor, Trans. Faraday Soc. 1948, 44, 376.
         | CrossRef | CAS |
      (b) B. P. Binks, W.-G. Cho, P. D. I. Fletcher, D. N. Tetsev, Langmuir 2000, 16, 1025.
         | CrossRef |

[22]  A. V. Cheprakov, N. V. Ponomareva, I. P. Beletskaya, J. Organomet. Chem. 1995, 486, 297.
         | CrossRef | CAS |

[23]  S. Shinoda, S. Friberg, Emulsions and Solubilization 1986 (Wiley: New York, NY).

[24]  E. Paetzold, G. Oehme, J. Mol. Catal. A – Chem. 2000, 152, 69.
         | CrossRef | CAS |

[25]  S. Mukhopadhyay, A. Yaghmur, M. Baidossi, B. Kundu, Y. Sasson, Org. Process Res. Dev. 2003, 7, 641.
         | CrossRef | CAS |

[26]  S. Mukhopadhyay, G. Rothenberg, N. Qafisheh, Y. Sasson, Tetrahedron Lett. 2001, 42, 6117.
         | CrossRef | CAS |

[27]  M. Lautens, J. Mancuso, H. Grover, Synthesis 2004, 2006.
         | CAS |

[28]  (a) G. Zou, Z. Wang, J. Zhu, J. Tang, Chem. Commun. 2003, 2438.
         | CrossRef | CAS |
      (b) A. Mori, Y. Danda, T. Fujii, K. Hirabayashi, K. Osakada, J. Am. Chem. Soc. 2001, 123, 10774.
         | CrossRef |

[29]  M. Hird, G. W. Gray, K. Toyne, Mol. Cryst. Liq. Cryst. 1991, 206, 187.
         | CrossRef | CAS |

[30]  V. Vashchenko, A. Krivoshey, I. Knyazeva, A. Petrenko, J. W. Goodby, Tetrahedron Lett. 2008, 49, 1445.
         | CrossRef | CAS |

[31]  D. Tsvelikhovsky, J. Blum, Eur. J. Org. Chem. 2008, 2017.

[32]  H. Nowothnick, J. Blum, R. Schomäcker, Angew. Chem. Int. Ed. 2011, 50, 1918.
         | CrossRef | CAS |


   
Subscriber Login
Username:
Password:  

 


    
Legal & Privacy | Contact Us | Help

CSIRO

© CSIRO 1996-2014