Synlett 2013; 24(4): 424-431
DOI: 10.1055/s-0032-1318103
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© Georg Thieme Verlag Stuttgart · New York

Hypervalent Iodine Reagents as Powerful Electrophiles

Authors

  • 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
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Publikationsverlauf

Received: 28. November 2012

Accepted after revision: 22. Dezember 2012

Publikationsdatum:
18. Januar 2013 (online)


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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