Issue 13, 2019

Boronic acid catalysis

Abstract

Although boronic acids are recognized primarily for their utility as reagents in transition metal-catalyzed transformations, other applications are emerging, including their use as reaction catalysts. Few methods are available for the catalytic activation of hydroxy functional groups as a way to promote their direct transformation into useful products under mild conditions. To this end, the ability of boronic acids to form reversible covalent bonds with hydroxy groups can be exploited to enable both electrophilic and nucleophilic modes of activation in various organic reactions. Using the concept of boronic acid catalysis (BAC), electrophilic activation of carboxylic acids leads to the formation of amides from amines, as well as cycloadditions and conjugate additions with unsaturated carboxylic acids. Alcohols can also be activated with boronic acid catalysts to form carbocation intermediates that can be trapped in selective Friedel–Crafts-type reactions with arenes and other nucleophiles. On the other hand, diols and saccharides can form tetrahedral adducts with boronic acids, which increases their nucleophilic character towards electrophiles. Altogether, BAC imparts mild and selective reaction conditions that display high atom-economy by circumventing the need for wasteful stoichiometric activation of hydroxy groups into halides or sulfonates.

Graphical abstract: Boronic acid catalysis

Article information

Article type
Tutorial Review
Submitted
12 Mac 2019
First published
15 Mei 2019

Chem. Soc. Rev., 2019,48, 3475-3496

Boronic acid catalysis

D. G. Hall, Chem. Soc. Rev., 2019, 48, 3475 DOI: 10.1039/C9CS00191C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements