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Synthesis of Alkynes and New Transformations Catalyzed by Gold(I) Complexes

Igor Jurberg 1 
1 ALIEN - Algebra for Digital Identification and Estimation
Inria Lille - Nord Europe, Inria Saclay - Ile de France, Centrale Lille, X - École polytechnique, CNRS - Centre National de la Recherche Scientifique : UMR8146
Abstract : The synthesis of alkynes using isoxazolones as precursors has been one of the methods studied by our laboratory in the last years. We have applied this methodology in the synthesis of 3-alkynylamides and their use to generate dihydropyrrolones. We have also developped new reactions catalyzed by Gold(I) complexes: the synthesis of 4-oxazol-2-ones from Boc-ynamides, a 1,5hydride/cyclization sequence affording carbocyclic ether structures and the formation of cinnoline derivatives. We have also developped a mechanistic study concerning the effect of two common counter-ions employed in gold-mediated cycloisomerization of 1,6-enynes: NTf2 and SbF6. The remote influence of the substituent on the alkene moiety was identified and studied in more detail. In the same way, a first investigation towards the identification of a catalyst allowing access to 6-membered cycles was performed (This outcome is less frequently observed, as 5-membered rings are usually obtained in these processes)
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Submitted on : Saturday, February 26, 2011 - 2:23:34 PM
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  • HAL Id : pastel-00570064, version 1



Igor Jurberg. Synthesis of Alkynes and New Transformations Catalyzed by Gold(I) Complexes. Catalysis. Ecole Polytechnique X, 2010. English. ⟨pastel-00570064⟩



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