Multicomponent Synthesis of β-Boryl Ketones Triggered by Ketene-Induced Metallate Rearrangement of Alkenylboronic Esters

Organic Letters 2026

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Authors: Haruki Mizoguchi, Atsuro Tanakura, Honoka Kokado, YOKO MISAKI, Masaki Bando, Yuya Kobashi, Akira Sakakura
DOI: 10.1021/acs.orglett.6c00987
Cited by: 1
References: 40

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.

Fields of Study & Subjects

Organoboron and organosilicon chemistry Catalytic Cross-Coupling Reactions Catalytic C–H Functionalization Methods

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
16
Pages
5147–5152
Publication date
10 April 2026
Language
EN