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Updated: Aug 6, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Enabling sulfur-centered nucleophiles in conjunctive coupling: triethylborane-mediated trifluoromethylation via
Sufal Paul1, Nayanthara T Anilkumar1, Eluvathingal D Jemmis2
1Department of Inorganic and Physical Chemistry, Indian Institute of Science Bengaluru.
Abstract:
A three-component conjunctive coupling reaction of vinylboronic esters has been developed via a 1,2-boronate rearrangement involving sulfur-centered nucleophiles to construct highly functionalized tertiary alkyl boronic esters. Togni-II has been used as the electrophilic source of the CF3 group in this reaction. A broad array of substrates containing various functional groups has been well accommodated with good to excellent isolated yields, retaining the valuable boronic ester moiety in the products, which can be subjected to further functionalization reactions. The mechanistic studies suggested the formation of a thiolate-coordinated boron 'ate' complex and the crucial role of the boron Lewis acid BEt3 in activating the Togni-II reagent. Density functional theory studies suggested that the interaction between the sp3-boronate complex and the Togni-II-BEt3 adduct triggers the 1,2-shift of the thiol moiety, which leads to the formation of the coupling product.
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