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Doctoral thesis
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Cu- and Pd-catalyzed Selective Transformations of (poly)enes

Imprimatur date2021-09-28
Defense date2021-09-06
Abstract

In the first part of this Thesis, we reported two ligand-controlled regiodivergent copper-catalyzed protoborations of 2-substituted [n]dendralenes (n = 3‒6). The dendralenes, a family of polyenes, are acyclic compounds with a geminal connection between the alkenes. The first copper-catalyzed methodology uses rac-BINAP and delivers product resulting from the protoboration of the terminal olefin. For the second reaction, a chiral phosphanamine ligand dictates the chemo- and regioselective borylation of the alkene cross-conjugated with the terminal olefin. In the second part of the Thesis, we described the development of a 3-step one-pot process. The first step is a palladium-catalyzed long-range isomerization of alkenyl ethers/amines into vinyl ethers/enamines. The second step is an intramolecular alkene-azide cycloaddition. The last step is a nitrogen extrusion reaction from 1,2,3-triazoline rings that provides 1,3-oxaza/1,3-diazaheterocycles. Each step was explored independently. Conditions found for the isomerization and for the cycloaddition/nitrogen extrusion reactions are not compatible in the one-pot process.

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Citation (ISO format)
DESFEUX, Camille Marie Odette. Cu- and Pd-catalyzed Selective Transformations of (poly)enes. 2021. doi: 10.13097/archive-ouverte/unige:155704
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Creation10/25/2021 8:06:00 AM
First validation10/25/2021 8:06:00 AM
Update time07/24/2023 10:11:59 AM
Status update07/24/2023 10:11:59 AM
Last indexation01/29/2024 10:51:03 PM
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