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Updated: May 30, 2025
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Merging Copper Catalysis with Nitro Allyl and Allyl Sulfone Derivatives: Practical, Straightforward, and Scalable
Nicolas Fincias1, Louis Clavier1, Cora Escande de Messières1
1Laboratoire de Synthèse Organique (LSO-UMR 7652) CNRS, Ecole Polytechnique, ENSTA-Paris, Institut Polytechnique de Paris 828 Bd des Maréchaux, 91128 Palaiseau Cedex, France.
Abstract:
We report here the first example of a copper-catalyzed transformation involving nitro allyl derivatives. This borylation reaction, which exploits the high versatility of the aforementioned precursor, tolerates a variety of functional groups and allows practical, scalable, and highly straightforward access to diversely substituted allylboronic esters in high yields. The method was also extended to allyl sulfones, which provides a very complementary approach, offering additional structural diversity along with improved stereoselectivities. This new reactivity was further exploited to synthesize γ-fluoroallyl boronic esters as well as various synthetically useful building blocks through key post-functionalizations. Both the reaction mechanism and the chemoselectivity were rationalized experimentally and through DFT calculations.
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