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Updated: Jun 4, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Pd-catalyzed borylative polycyclization of enediynes to alkylboronates
Juan Marco-Martínez1, Elena Buñuel, Ruth López-Durán
1Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Madrid, Spain.
Abstract:
Pd-catalyzed bicyclization of 1-ene-6,11-diynes with bis(pinacolato)diboron smoothly affords synthetically useful homoallylic alkylboronates under mild conditions, avoiding the use of highly nucleophilic or basic reagents. One C-B bond and two new C-C bonds are created, and two new stereogenic centers are stereospecifically formed in a single tandem operation. The obtained products suggest a cascade reaction in which the last step is the transmetalation of bis(pinacolato)diboron, this being faster than a possible β-hydride elimination process. The reaction is general and has been applied to enediynes with different substituents on the alkene unit, the bridging groups, and the alkyne moiety. The bicyclized alkylboronates thus obtained can be functionalized by oxidation to alcohols, formation of trifluoroborate salts, or by Suzuki coupling reactions.
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