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Updated: Jun 7, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Csp-H/F bond activation and borylation with iron
Ethan Zars1, Lisa Pick2, Achala Kankanamge1
1Department of Chemistry, University of Pennsylvania, 231 S 34th St, Philadelphia, PA 19104, USA. mindiola@sas.upenn.edu.
Abstract:
Reduction of [K2{(pyrr2pyr)Fe}2(μ-N2)] (1) with two equiv. of KC8 in the presence of crown-ether 18-C-6 yields the N2 adduct [{K(18-C-6)}2(pyrr2pyr)Fe(N2)] (2). Complex 2 heterolytically splits the Csp-H bond of benzene to form [{K(18-C-6)}(pyrr2pyr)Fe(C6H5)] (3), whereby usage of a diboron B2pin2 promotes hydride elimination to form the salt [K(18-C-6)HB2Pin2] (4). Similarly, 3 can also be formed by cleavage of the C-F bond of fluorobenzene. Reaction of 3 with ClBcat yields [K(18-C-6)(thf)2][(pyrr2pyr)FeCl] (5) and PhBcat and the former can be reduced to 2 to complete a synthetic cycle for heterolytic benzene C-H activation and borylation.
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