A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates

2009/04/30 by David M. Knapp, Eric P. Gillis, Martin D. Burke · 3 citations
Chemistry · #Catalytic Cross-Coupling Reactions #Catalytic C–H Functionalization Methods #Organoboron and organosilicon chemistry

paper · doi:10.1021/ja901416p

openalex publication_date 2009/04/30 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01

Abstract

Many boronic acids, including 2-heterocyclic, vinyl, and cyclopropyl derivatives, are inherently unstable, which can limit their benchtop storage and/or efficient cross-coupling. We herein report the first general solution to this problem: in situ slow release of unstable boronic acids from the corresponding air-stable MIDA boronates. This remarkably general approach has transformed all three classes of these unstable boronic acids into shelf-stable and highly effective building blocks for cross-coupling with a wide range of aryl and heteroaryl chlorides.

Citations

• Organotrifluoroborates: Protected Boronic Acids That Expand the Versatility of the Suzuki Coupling Reaction
• Copper-Facilitated Suzuki Reactions: Application to 2-Heterocyclic Boronates

Cited by

• The Slow‐Release Strategy in Suzuki–Miyaura Coupling
• Structure, Properties, and Preparation of Boronic Acid Derivatives
• Protodeboronation [wikipedia]