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

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
Further Information

Publication History

Received: 28 November 2012

Accepted after revision: 22 December 2012

Publication Date:
18 January 2013 (online)


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