La catalyse au palladium pour l'obtention d'indoles fonctionnalisés : application à une synthèse monotope d'indoloquinones par catalyse hétérogène

Abstract : Since the beginning of the 90's, the Larock heteroannulation became a method of choice to afford, in a single step, 2,3-disubstituted indoles. While effective, this methodology suffered of drawbacks lied to the use of salts, additives and homogeneous catalyst. Thus, we developed the first ligand and salt free heterogeneous Larock heteroannulation. Different commercially available, home made catalysts (Pd/C or [Pd]/NaY) or new palladium complexes immobilised onto mesoporous silica SBA-15 were evaluated. Surprisingly, this methodology allowed an activation of the 2-bromoanilines without using additives. Another procedure to obtain indole nucleus emerged over the past few years as an outstanding alternative to traditional cross-coupling reactions: namely the "direct arylation". Despite major improvements, no report focuses on complementary C2 and C3-arylation procedures by means of a unique catalytic system. Herein, we describe an innovative "on water" palladium-catalyzed C-H arylation of (NH)-indoles that is site-selective through a base/halide-controlled using cheap reagents. This methodology allows the preparation of either C2- or C3-arylindoles with high isolated yields. Finally, as part of our project related to syntheses of high added value products by heterogeneous catalysis, we investigated studies in order to obtain pyrroloiminoquinones. This new methodology using only two steps will permit an access to numerous bioactive analogues.
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Other. Université Claude Bernard - Lyon I, 2010. French. <NNT : 2010LYO10195>


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Nelly Batail. La catalyse au palladium pour l'obtention d'indoles fonctionnalisés : application à une synthèse monotope d'indoloquinones par catalyse hétérogène. Other. Université Claude Bernard - Lyon I, 2010. French. <NNT : 2010LYO10195>. <tel-00713118>

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