Hypervalent Iodine(III) in Direct Carbon–Hydrogen Bond Functionalization

Rishikesh Narayan; Srimanta Manna; Andrey P. Antonchick

doi:10.1055/s-0034-1379912

Synlett, Table of Contents

Synlett 2015; 26(13): 1785-1803
DOI: 10.1055/s-0034-1379912

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Hypervalent Iodine(III) in Direct Carbon–Hydrogen Bond Functionalization

Rishikesh Narayan

^aDepartment of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Str. 11, 44227 Dortmund, Germany Email: Andrey.Antonchick@mpi-dortmund.mpg.de

,

Srimanta Manna

^aDepartment of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Str. 11, 44227 Dortmund, Germany Email: Andrey.Antonchick@mpi-dortmund.mpg.de

^bDepartment of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn Str. 6, 44227 Dortmund, Germany

,

Andrey P. Antonchick*

^aDepartment of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Str. 11, 44227 Dortmund, Germany Email: Andrey.Antonchick@mpi-dortmund.mpg.de

^bDepartment of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn Str. 6, 44227 Dortmund, Germany

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Abstract

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Abstract

Direct methods of novel bond formation through functionalization of nonreactive carbon–hydrogen bonds represent an efficient synthetic approach. Cross-dehydrogenative coupling has emerged as an area of huge potential and importance for novel bond formation. The application of hypervalent iodine(III) reagents in direct carbon–hydrogen bond functionalization reactions is of immense interest because the functionalization of the nonreactive carbon–hydrogen bonds proceeds under metal-free reaction conditions. This account covers recent developments in the area of hypervalent iodine(III) mediated direct carbon–hydrogen bond functionalization.

1 Introduction

2 Intramolecular Amination for Carbazole Synthesis

3 Intermolecular Amination

4 Intermolecular Annulation

5 Intermolecular Nucleophilic Amination

6 Hypervalent Iodine(III) Mediated Radical Reactions

6.1 Cross-Dehydrogenative Coupling of a Heterocycle and an Aldehyde

6.2 Cross-Dehydrogenative Coupling of a Heterocycle and an Alkane

6.3 Intramolecular Cyclization

7 Conclusion

Key words

hypervalent iodine - aminations - heterocycles - organocatalysis - cross-dehydrogenative coupling

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References

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