Nitrogen-Centered Radical Scavengers

Sarah B. Höfling; Markus R. Heinrich

doi:10.1055/s-0030-1258305

REVIEW

Nitrogen-Centered Radical Scavengers

Sarah B. Höfling, Markus R. Heinrich*
Department für Chemie und Pharmazie, Professur für Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen, Germany
Fax: +49(9131)8522585; e-Mail: Markus.Heinrich@medchem.uni-erlangen.de;

Abstract

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Abstract

As reactants in radical reactions, nitrogen-centered scavengers can offer valuable alternatives to ionic methods regarding the synthesis of nitrogen-containing compounds. In this review article, we present developments, scope, limitations and future challenges in this field of radical chemistry.

1 Introduction

2 Alkyl Azides

3 Sulfonyl Azides

3.1 Reactions with Alkyl Radicals

3.2 Functionalization of Alkenes

3.3 Diastereoselective Reactions

3.4 Natural Product Synthesis

4 Arenediazonium Salts

4.1 Reactions with Alkyl Radicals

4.2 Functionalization of Alkenes

4.3 Functionalization of Arenes

5 Azo Compounds

5.1 Intramolecular Addition

5.2 Diazirines

5.3 Azo Dicarboxylates

6 Nitrogen Monoxide and Synthetic Equivalents

6.1 Nitrogen Monoxide

6.2 Thionitrosyl Esters

6.3 Alkyl Nitrites

7 Imines

7.1 Intramolecular Addition

7.2 Stannylimines

8 Hydrazines

9 Conclusion

Key words

radicals - radical reaction - azides - azo compounds - imines

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