Metal-free Oxidative Cross-Coupling Reaction of Aromatic Compounds Containing Heteroatoms

Published as part of the ISHC Conference Special Section

Abstract

The biaryl unit containing a heteroatom is a key structure in a large number of natural products and π-conjugated organic systems. The cross-couplings can provide powerful methods for the construction of biaryls and heterobiaryls; thus the development of a new coupling method has been intensively studied by synthetic chemists. Therefore, the oxidative biaryl coupling reaction of arenes containing a heteroatom is a significantly attractive, convenient, and straightforward route to the synthesis of biaryls due to its operational simplicity avoiding the preparation of the corresponding halogenated and metallated arenes. In this report, recent progress in the field of metal-free oxidative cross-coupling reactions of aromatic compounds using hypervalent iodine(III) reagents, is presented.

1 Introduction

2 Cyanation and Halogenation Reactions of Heteroaromatic Compounds

3 Biaryl Coupling Reaction of Heteroaromatic Compounds

3.1 Regioselective Coupling Reaction of Thiophenes

3.2 Cross-Coupling Reaction of Thiophenes

3.3 Coupling Reaction of EDOT and Pyrroles

3.4 Cross-Coupling Reaction of Pyrroles

4 Cross-Coupling Reaction of Anilines

5 Cross-Coupling Reaction of Phenols

6 Cross-Coupling Reaction of N-Heteroaromatics with Aryl Radicals from Diaryliodonium(III) Salts

7 Conclusion

Key words

cross-coupling - iodine - heteroatom - metal-free - aromatic compound

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