Hypervalent Iodine Reagents as Powerful Electrophiles

Michael Brown; Umar Farid; Thomas Wirth

doi:10.1055/s-0032-1318103

Synlett, Table of Contents

Synlett 2013; 24(4): 424-431
DOI: 10.1055/s-0032-1318103

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Hypervalent Iodine Reagents as Powerful Electrophiles

Michael Brown

Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK Fax: +44(29)20876968 Email: wirth@cf.ac.uk

,

Umar Farid

Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK Fax: +44(29)20876968 Email: wirth@cf.ac.uk

,

Thomas Wirth*

Cardiff University, School of Chemistry, Park Place, Cardiff CF10 3AT, UK Fax: +44(29)20876968 Email: wirth@cf.ac.uk

› Author Affiliations

Abstract

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Abstract

Hypervalent iodine reagents have been investigated as very powerful electrophiles in many different reactions. Efficient formation of new carbon–heteroatom bonds as well as carbon–carbon bonds can be achieved typically under mild reaction conditions with these metal-free reagents. Enantiomerically pure reagents provide the potential for stereoselective reactions and this aspect is highlighted in this account.

1 Introduction

2 Stereoselective Reactions

3 Reactions with Alkenes

3.1 Iodolactonizations

3.2 Oxyaminations of Alkenes

3.3 Aziridinations of Alkenes

4 α-Functionalization of Carbonyl Compounds and Catalysis

5 Rearrangements

6 Arylations

7 Oxidations

8 Summary and Outlook

Key words

alkenes - catalysis - electrophiles - hypervalent iodine - stereoselective synthesis

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