Synthesis of Heterobiaryls Featuring 1,4 N···S Inter-Ring Interactions

David Tilly; Floris Chevallier; Florence Mongin

doi:10.1055/s-0035-1560360

Synthesis, Table of Contents

Synthesis 2016; 48(02): 184-199
DOI: 10.1055/s-0035-1560360

short review

Synthesis of Heterobiaryls Featuring 1,4 N···S Inter-Ring Interactions

David Tilly

Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1 – CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes, France Email: floris.chevallier@univ-rennes1.fr Email: florence.mongin@univ-rennes1.fr

,

Floris Chevallier*

Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1 – CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes, France Email: floris.chevallier@univ-rennes1.fr Email: florence.mongin@univ-rennes1.fr

,

Florence Mongin*

Chimie et Photonique Moléculaires, Institut des Sciences Chimiques de Rennes, UMR 6226, Université de Rennes 1 – CNRS, Bâtiment 10A, Case 1003, Campus de Beaulieu, Avenue du Général Leclerc, 35042 Rennes, France Email: floris.chevallier@univ-rennes1.fr Email: florence.mongin@univ-rennes1.fr

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Abstract

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Abstract

Because of its low-lying σ* orbitals, the C–S bond can interact with electron donors. In this short review, our goal is to focus on intramolecular interactions between bivalent sulfur and basic nitrogen atoms. In particular, we will consider the synthesis of selected heterobiaryls for which 1,4 N···S inter-ring interactions can be identified from X-ray diffraction data. Finally, we will briefly touch on the use of such conformational preferences in various applications.

1 Introduction

2 Cross-Coupling with C–C Bond Formation

3 Cross-Coupling with C–N Bond Formation

4 Nucleophilic Addition to Azine Followed by Oxidation

5 Multicomponent Reactions

6 Heterobiaryl Formation by Azine Building

7 Heterobiaryl Formation by Building of the Sulfur-Containing Heterocycle

8 Cycloaddition Reactions

9 Other Syntheses

10 Conclusion

Key words

heterobiaryls - nitrogen - sulfur - azines - heterocycles - cross-coupling - X-ray diffraction

Full Text

References

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