Development of new copper-assisted domino reactions for insertion of fluoroalkyl groups

Marghem, Gilles
(2026)

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Authors
Supervisors
Leyssens, Tom  
 ;
Riant, Olivier  
Abstract
(en) Various projects were tackled during this thesis. The first part is devoted to copper-catalyzed cascade reactions. As Prof. Riant and Leyssens' laboratory has a certain mastery/expertise in the field of borocupration cascade reactions, it was decided to attempt to carry out borotrifluoromethylation and borotrifluoromethylthiolation reactions of allene via the activation of a copper catalyst. The challenge in this main objective lies mainly in the regioselectivity of allene addition, which can lead to up to 6 possible products, but also in the high oxidizing power of the trifluoromethylating / trifluoromethylthiolating agents. This section has been divided into two parts, one devoted specifically to the use of SCF3 type precursors and the other to the use of CF3 type groups. The second chapter of this thesis focuses on an unusual substrate, 4-alkylidene-isoxazolin-5-one derivatives. These compounds are precursors of carbon-carbon triple bonds, thanks to a reaction called nitrosative cleavage, which remains a difficult chemical function to access and has great synthetic appeal. This substrate has the characteristics of a Michael acceptor and is therefore very interesting to combine copper chemistry for enantioselective or non-enantioselective 1,4-type additions. The primary objective is to carry out a 1,4-hydroboration reaction on a 4-alkylidene-isoxazolin-5-one compound using a copper catalyst. Finally, the third chapter discusses a photoacylation reaction of aldehyde on same specific substrate uses in chapter 2 (4-alkylidene-isoxazolin-5-one). The products obtained can lead to furan, propargyl ketones or allenyl ketone derivatives.
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Marghem, G. (2026). Development of new copper-assisted domino reactions for insertion of fluoroalkyl groups. https://hdl.handle.net/2078.5/276564