Synlett 2015; 26(13): 1785-1803
DOI: 10.1055/s-0034-1379912
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© Georg Thieme Verlag Stuttgart · New York

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

Rishikesh Narayan
a   Department 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
a   Department of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Str. 11, 44227 Dortmund, Germany   Email: Andrey.Antonchick@mpi-dortmund.mpg.de
b   Department of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn Str. 6, 44227 Dortmund, Germany
,
Andrey P. Antonchick*
a   Department of Chemical Biology, Max Planck Institute for Molecular Physiology, Otto-Hahn Str. 11, 44227 Dortmund, Germany   Email: Andrey.Antonchick@mpi-dortmund.mpg.de
b   Department of Chemistry and Chemical Biology, Technische Universität Dortmund, Otto-Hahn Str. 6, 44227 Dortmund, Germany
› Author Affiliations
Further Information

Publication History

Received: 10 February 2015

Accepted after revision: 18 March 2015

Publication Date:
20 May 2015 (online)


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