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Pd-catalyzed domino carbonylative/decarboxylative allylation

Abstract : The present thesis work dealt with the development on new palladium-catalyzed pseudo-domino sequences. A first pseudo-domino type I process featuring a carbonylation / decarboxylative allylation was designed with α-chloroacetophenone. The sequence allowed the selective monoallylation of readily available α-chloroketones derivatives in one single synthetic operation. This pseudo-domino sequence could be applied to variously substituted acetophenones. We also designed a three-step pseudo-domino reaction featuring N-allylation / carbopalladation / carbonylation. This sequence allowed us to prepare substituted indolines in one single synthetic operation from readily available substrates. The extension to a four step pseudo-domino sequence was also envisaged. Switching the alcohol used to allyl alcohol should merge both sequences, by adding a decarboxylative allylation step to the three-step process
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Submitted on : Monday, June 3, 2013 - 1:51:23 PM
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  • HAL Id : tel-00829489, version 1

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Steven Giboulot. Pd-catalyzed domino carbonylative/decarboxylative allylation. Organic chemistry. Université Pierre et Marie Curie - Paris VI, 2012. English. ⟨NNT : 2012PAO66196⟩. ⟨tel-00829489⟩

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