Issue 24, 2014

Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

Abstract

Investigation of new methods for the synthesis of C–C bonds is fundamental for the development of new organic drugs and materials. Aryl-, alkenyl- and alkynylboronic acids and their derivatives constitute attractive reagents towards this end, due to their stability, low toxicity and ease of handling. However, these compounds are only moderately nucleophilic. Consequently, the most popular C–C bond forming reactions of these boronic acids, such as the Suzuki–Miyaura, Heck, and Hayashi–Miyaura reactions, or additions to C[double bond, length as m-dash]O and C[double bond, length as m-dash]N bonds, require catalysis by transition metals. However, due to the toxicity and cost of transition metals, some new methods for C–C bond formation using aryl-, alkenyl- and alkynylboronic acids under transition-metal-free conditions are beginning to emerge. In this tutorial review, the recent synthetic advances in this field are highlighted and discussed.

Graphical abstract: Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

Article information

Article type
Tutorial Review
Submitted
09 Jun 2014
First published
03 Sep 2014

Chem. Soc. Rev., 2014,43, 8215-8225

Author version available

Transition-metal-free C–C bond forming reactions of aryl, alkenyl and alkynylboronic acids and their derivatives

S. Roscales and A. G. Csákÿ, Chem. Soc. Rev., 2014, 43, 8215 DOI: 10.1039/C4CS00195H

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