Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Saverio Florio; Antonio Salomone

doi:10.1055/s-0035-1561596

Synthesis, Table of Contents

Synthesis 2016; 48(13): 1993-2008
DOI: 10.1055/s-0035-1561596

short review

Heterocycle-Mediated ortho-Functionalization of Aromatic Compounds: The DoM Methodology and Synthetic Utility

Authors

Saverio Florio*

^aCINMPIS Consortium, Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari, Via E. Orabona 4, 70125 Bari, Italy Email: saverio.florio@uniba.it
Antonio Salomone

^aCINMPIS Consortium, Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari, Via E. Orabona 4, 70125 Bari, Italy Email: saverio.florio@uniba.it

^bDipartimento di Scienze e Tecnologie Biologiche e Ambientali, Università del Salento, Prov.le Lecce-Monteroni, 73100 Lecce, Italy

Abstract

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Abstract

The directed ortho-lithiation of substituted aromatics containing a small-ring heterocycle as a directing metalating group is described. The reaction of the ortho-lithiated intermediates with electrophiles gives successfully the corresponding substituted derivatives. This brief review highlights the importance of heterocyclic systems as directed metalation groups (DMG) in the regioselective lithiation of simple aromatic compounds. The utility of the synthetic elaboration of the heterocyclic moiety is also stressed. It is possible to access interesting molecules by combining DoM methodology with Negishi or Suzuki–Miyaura cross-coupling protocols.

1 Introduction

2 Lithiation of Aryl-Substituted O-Heterocycles

3 Lithiation of Aryl-Substituted N-Heterocycles

4 Lithiation of Five-Membered Arylheterocycles

5 Conclusion

Key words

arenes - cross-coupling - heterocycles - lithiation - regioselectivity

Full Text

References

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