Iminoiodanes and C-NBond Formation in Organic Synthesis

Philippe Dauban; Robert H. Dodd

doi:10.1055/s-2003-41010

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Synlett 2003(11): 1571-1586
DOI: 10.1055/s-2003-41010

ACCOUNT

Iminoiodanes and C-NBond Formation in Organic Synthesis

Philippe Dauban*, Robert H. Dodd*
Institut de Chimie des Substances Naturelles, C. N. R. S., 91198 Gif-sur-Yvette Cedex, France
Fax: +33(1)69077247; e-Mail: Philippe.Dauban@icsn.cnrs-gif.fr; e-Mail: Robert.Dodd@icsn.cnrs-gif.fr;

Further Information

Publication History

Received 3 December 2002
Publication Date:
11 August 2003 (online)

Abstract
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Abstract

Structurally related to iodosylbenzene PhI=O, iodonium imidesPhI=NR, off-white to pale yellow solids of low solubility, belongto the class of hypervalent iodine(III) reagents and were first preparednearly thirty years ago. Two additional decades were needed beforethey could be considered as useful nitrene precursors with the discoveryof the copper-catalyzed aziridination of olefins. Since then, iminoiodaneshave been successfully applied in the total synthesis of naturaland/or biologically active compounds. Recent developmentsaimed at circumventing their tedious preparation led to the discoveryof one-pot nitrogen transfers from sulfonamides, sulfamates, orcarbamates mediated by iodosylbenzene(diacetate) PhI(OAc)₂ oriodosylbenzene. Reliable functionalizations of alkanes and alkenesvia C-H insertion or aziridination using copper or rhodiumcatalysts can now be considered as synthetically useful processes.

1 Introduction
2 Iminoiodanes
2.1 General Properties
2.2 Methods of Preparation
2.3 Types of N-SubstitutedIminoiodanes
3 Iminoiodanes in Organic Synthesis
3.1 Natural Product Synthesis
3.2 Synthesis of Biologically Active Compounds
4 Recent Developments: Iodonium Ylides as in situ
Intermediates
4.1 Metalloporphyrin-Mediated Nitrogen Atom Transfer
4.2 Rhodium-Catalyzed Nitrogen Atom Transfer
4.3 Copper-Catalyzed Nitrogen Atom Transfer
5 Conclusion and Future Prospects

Key words

hypervalent iodine - iminoiodane - iodosylbenzene - iodosylbenzene diacetate - nitrene - aziridination - C-H insertion - copper catalyst - rhodiumcatalyst - total synthesis

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