Related Experiment Video
Updated: Apr 11, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
Published on: May 26, 2019
Multicomponent Synthesis of β-Boryl Ketones Triggered by Ketene-Induced Metallate Rearrangement of Alkenylboronic
Haruki Mizoguchi1, Atsuro Tanakura1, Honoka Kokado1
1Graduate School of Environmental, Life, Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Kita-ku, Okayama 700-8530, Japan.
Abstract:
A four-component coupling of alkenylboronic esters, organolithium reagents, ketenes, and heteroatomic electrophiles yielding highly substituted tertiary β-boryl ketones is described. The reaction proceeds via ketene-triggered metallate rearrangement of alkenylboronic ester ate-complexes and subsequent electrophilic trapping of the resulting boron enolate, forming two carbon-carbon bonds and one carbon-heteroatom bond. This method provides expeditious access to diverse β-boryl carbonyl derivatives from simple building blocks.
More Related Videos
Related Concept Videos
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.
Aldol Condensation with β-Diesters: Knoevenagel Condensation
α-Alkylation of Ketones via Enolate Ions
Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Reactions of Aldehydes and Ketones: Baeyer–Villiger Oxidation
The carbonyl center is activated by...
Hydroboration-Oxidation of Alkenes

