A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates.
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.
Knapp
David M
DM
Roger Adams Lab, Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA.
Gillis
Eric P
EP
Burke
Martin D
MD
D001897:Boronic Acids / Q000737:chemistry*; D004355:Drug Stability; D007098:Imino Acids / Q000737:chemistry*; D014867:Water / Q000737:chemistry
D001897:Boronic Acids; D007098:Imino Acids; C533766:N-methyliminodiacetic acid; D014867:Water