Synthesis 2016; 48(02): 184-199
DOI: 10.1055/s-0035-1560360
short review
© Georg Thieme Verlag Stuttgart · New York

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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Publikationsverlauf

Received: 27. August 2015

Accepted after revision: 05. Oktober 2015

Publikationsdatum:
03. November 2015 (online)


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

 
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