Related Experiment Video
Updated: Sep 24, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
A deprotonation pathway to reactive [B]CH2 boraalkenes
Karel Škoch1, Chaohuang Chen1, Constantin G Daniliuc1
1Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraβe 40, 48149 Münster, Germany. erker@uni-muenster.de.
Abstract:
The BH compounds IMes(ArF)BH(NTf2) (ArF: C6F5 or FpXyl) were converted to the IMes(ArF)BCH2 boraalkenes in a three step reaction sequence of B-methylation with methyllithium, hydride abstraction and deprotonation. The BCH2 boraalkenes reacted with elemental sulfur to give a thiaborirane product. They underwent [2+2] cycloaddition reactions with carbon dioxide or sulfur dioxide to give four-membered boron containing heterocycles. The boraalkenes added strongly Lewis acidic boranes at their CH2 carbon atoms. The corresponding HB(C6F5)2/boraalkene adduct reduced carbon monoxide to a -OCH(C6F5)- moiety inside a five-membered heterocycle at the B-CH2-B template. The boraalkenes reacted with the [(Me2S)AuCl] reagent to form the corresponding (boraalkene)AuCl complexes.
Related Concept Videos
Hydroboration-Oxidation of Alkenes
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
Regioselectivity and Stereochemistry of Hydroboration
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
α-Alkylation of Ketones via Enolate Ions
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Radical Anti-Markovnikov Addition to Alkenes: Overview

