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Emerging approaches for the synthesis of triazoles: beyond metal-catalyzed and strain-promoted azide-alkyne cycloaddition

Lima, Carolina G. S ; Ali, Akbar ; van Berkel, Sander S ; Westermann, Bernhard ; Paixão, Márcio W

Chemical communications (Cambridge, England), 2015-07, Vol.51 (54), p.1784-1796 [Periódico revisado por pares]

England

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  • Título:
    Emerging approaches for the synthesis of triazoles: beyond metal-catalyzed and strain-promoted azide-alkyne cycloaddition
  • Autor: Lima, Carolina G. S ; Ali, Akbar ; van Berkel, Sander S ; Westermann, Bernhard ; Paixão, Márcio W
  • Assuntos: Alkynes - chemistry ; Assembly ; Azides - chemistry ; Biological ; Catalysis ; Click Chemistry ; Cycloaddition ; Cycloaddition Reaction ; Formations ; Isomerism ; Ketones - chemistry ; Metals - chemistry ; Synthesis ; Triazoles ; Triazoles - chemical synthesis ; Triazoles - chemistry
  • É parte de: Chemical communications (Cambridge, England), 2015-07, Vol.51 (54), p.1784-1796
  • Notas: Márcio Weber Paixão was born in Cachoeira do Sul, RS, Brazil, in 1979. He received his BS in Chemistry in 2003 from the Federal University of Santa Maria (Brazil). In 2007, he completed his PhD at the same university under the supervision of Prof. A. L. Braga, working with catalytic enantioselective synthesis. He immediately started postdoctoral studies at the University of São Paulo (Brazil) and then at the Center for Catalysis, University of Aarhus, DK, where he worked under guidance of Prof. Karl A. Jørgensen. Since 2010 he has started his independent career at the Federal University of São Carlos, Brazil. In 2012 he worked as visiting professor in the Group of Prof. Carlos F. Barbas III at The Scripps Research Institute (TSRI). His research interests focus on the development of new catalytic methodologies.
    Akbar Ali is currently working as a PhD fellow at Federal University of São Carlos, Brazil under the guidance of Prof. Dr Marcio Weber Paixão. He completed his Master in the subject of organic chemistry from University of Malakand K.P.K Pakistan in 2007 and then his MPhil in the same subject from Hazara University K.P.K Pakistan in 2011 under the supervision of Prof. Dr Wajid Rehman and cosupervisor Prof. Dr Muhammad Raza Shah (International Centre for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry. W.H.O. Collaborating Centre University of Karachi, Pakistan). His interests include organic synthesis, click chemistry and asymmetric organocatalysis.
    Dr Sander S. van Berkel received his MSc degree in Organic Chemistry at Radboud University Nijmegen, the Netherlands, in 2003. Under the supervision of Prof. Dr Floris Rutjes he received his PhD degree in 2008 for his work on developing tools for monitoring thrombine generation. He then moved to the Leibniz-Institute of Plant Biochemistry in Halle, Germany, for a postdoctoral stay in the group of Prof. Dr L. A. Wessjohann working on natural product synthesis. He held a position as postdoctoral fellow at the University of Oxford working on novel non-invasive cancer imaging strategies.
    Prof. Dr Bernhard Westermann obtained his Diploma degree at the University of Paderborn (Germany, Prof. F. Seela). At the same university, he received his PhD in 1989, working with Prof. W. Sucrow and H.-J. Altenbach. After a postdoctoral stay at the University of Toronto (Prof. J. B. Jones) from 1990 to 1991, he started his independent scientific career at the University of Paderborn mentored by Prof. K. Krohn. After his habilitation in 1998, he stayed at this university as an associate professor. In 2004 he moved to the Leibniz-Institute of Plant Biochemistry, where he continues to work on topics dealing with natural product synthesis, method development with regard to multicomponent reactions, and ligation strategies.
    Carolina Lima obtained her Bachelor in Chemistry degree in 2010 from Federal University of Goiás, Brazil and MS in Chemistry in 2012, from the same university. In 2012 she joined Paixão's group at Federal University of São Carlos, Brazil, where she is currently conducting her PhD studies. Her research interests include "semi-heterogeneous" catalysis, organic synthesis and green chemistry, as well as asymmetric organocatalysis.
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  • Descrição: Metal-free 1,3-dipolar cycloaddition reactions have proven to be a powerful tool for the assembly of key heterocycles, in particular diversely functionalized 1,2,3-triazoles. A number of metal-free (3+2)-cycloaddition approaches have been developed up to date with the aim to circumvent the use of metal catalysts allowing these reactions to take place in biological systems without perturbation of the naturally occurring processes. This feature article specifically provides an overview of emerging metal-free synthetic routes, and their mechanistic features, in the formation of functionalized 1,2,3-triazoles. Organocatalytic click reactions to 1,4- and 1,5-disubstituted triazoles are rapidly emerging as most valuable alternatives to other triazole-forming protocols. Here the latest developments are discussed leading to intriguing synthetic possibilities.
  • Editor: England
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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