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Updated: Mar 24, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Iridium(I)-catalyzed C-H Borylation of α,β-Unsaturated Esters with Bis(pinacolato)diboron
Ikuo Sasaki1, Jumpei Taguchi1, Hana Doi1
1Division of Chemical Process Engineering and, Frontier Chemistry Center (FCC), Graduate School of Engineering, Hokkaido University, Kita 13 Nishi 8, Kita-ku, Sapporo, Hokkaido, 060-8628, Japan), Fax: (+81) 11-706-6562.
Abstract:
A new process has been developed for the iridium(I)-catalyzed vinylic C-H borylation of α,β-unsaturated esters with bis(pinacolato)diboron (B2 pin2 ). These reactions proceeded in octane at temperatures in the range of 80-120 °C to afford the corresponding alkenylboronic compounds in high yields with excellent regio- and stereoselectivities. The presence of an aryl ester led to significant improvements in the yields of the acyclic alkenylboronates. Crossover experiments involving deuterated substrates as well as a mixture of stereoisomers confirmed that this reaction proceeds via a 1,4-addition/β-hydride elimination mechanism. Notably, this reaction was also used to develop a one-pot borylation/Suzuki-Miyaura cross-coupling procedure.
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