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Synthesis 2003(4): 0469-0483
DOI: 10.1055/s-2003-37721
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© Georg Thieme Verlag Stuttgart · New York

The Synthesis and Applications of Heterocyclic Boronic Acids

Elizabeth Tyrrell*a, Phillip Brookesb
a School of Chemical and Pharmaceutical Sciences, Kingston University, Penrhyn Road, Kingston, Surrey, KT1 2EE, England.
e-Mail: e.tyrrell@kingston.ac.uk.;
b Maybridge plc, Trevillett, Tintagel, Cornwall, PL34 0HW, England.
Further Information

Publication History

Received 22 October 2002
Publication Date:
07 March 2003 (online)

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Abstract

Boronic acids are valued by organic chemists for their important role in the synthesis of biphenyls via a palladium(0) catalysed cross-coupling reaction with aryl halides (Suzuki reaction). Despite their synthetic utility and known biological activities heterocyclic boronic acids feature less frequently often due to difficulties in their synthesis. This paper provides an overview of the synthesis and applications of a range of heterocyclic boronic acids.

1 Introduction

2 Nitrogen Heterocycles

2.1 Pyridinylboronic Acids

2.1 1 2-Pyridinylboronic Acid

2.1 2 3- and 4-Pyridinylboronic Acid

2.2 Pyrrolylboronic Acids

2.2.1 Pyrrole-2-boronic Acid

2.2.2 Pyrrole-3-boronic Acid

2.3 Indolylboronic Acids

2.3.1 Indol-2-ylboronic Acid

2.3.2 Indol-3-ylboronic Acid

2.3.3 5/6/7-Indolylboronic Acid

2.4 Imidazolylboronic Acids

2.5 Quinolinylboronic Acids

2.6 Pyrimidinylboronic Acids

3 Sulfur Heterocycles

3.1 Thienylboronic Acids

3.1.1 2-Thienylboronic Acid

3.1.2 3-Thienylboronic Acids

3.2 Benzothiophenylboronic Acids

4 Oxygen Heterocycles

4.1 Furylboronic Acids

4.1.1 2-Furylboronic Acid

4.1.2 3-Furylboronic Acid

4.2 Benzofuranylboronic Acids

5 Conclusions

Key words

Suzuki reaction - heterocyclic boronic acids - palladium(0) catalysed cross-coupling - trialkylboranes - lithium-halogen exchange

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Products for Suzuki Coupling Aldrich ChemFiles 2001, 1