Synthesis 2011(4): 517-538  
DOI: 10.1055/s-0030-1258328
REVIEW
© Georg Thieme Verlag Stuttgart ˙ New York

α-Functionalization of Carbonyl Compounds Using Hypervalent Iodine Reagents

Eleanor A. Merritt, Berit Olofsson*
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden
Fax: +46(8)154908; e-Mail: berit@organ.su.se;
Further Information

Publication History

Received 19 September 2010
Publication Date:
15 November 2010 (online)

Abstract

α-Functionalized carbonyl compounds are versatile intermediates in organic synthesis. A broad range of both carbon and heteroatom substituents can be introduced into the α-position of carbonyl compounds using hypervalent iodine reagents. Herein we summarize the use of these environmentally benign reagents with particular emphasis on catalytic and asymmetric methodology developed over the past decade.

1 Introduction

2 Oxygenation

3 Halogenation

4 Trifluoromethylation

5 Arylation

6 Alkynylation and Alkenylation

7 Homocoupling

8 Functionalization of α,β-Unsaturated Carbonyl Compounds

9 Miscellaneous

10 Summary