Recent advances in hypervalent iodine(III)-catalyzed functionalization of alkenes

Xiang Li,Guosheng Liu,Pinhong Chen

doi:10.3762/bjoc.14.154

Xiang Li, Guosheng Liu + Show 1 more

Open Access

https://doi.org/10.3762/bjoc.14.154

Copy DOI

Abstract

Hypervalent iodine(III) reagents have been well-developed and widely utilized in functionalization of alkenes, however, generally either stoichiometric amounts of iodine(III) reagents are required or stoichiometric oxidants such as mCPBA are employed to in situ generate iodine(III) species. In this review, recent developments of hypervalent iodine(III)-catalyzed functionalization of alkenes and asymmetric reactions using a chiral iodoarene are summarized.

Highlights

Hypervalent iodine(III) reagents, named as λ3-iodanes, have been widely used in organic synthesis since the 1990s, due to their stability, low toxicity and mild reaction conditions [1,2,3,4,5,6,7,8,9,10]
Due to our interest in the functionalization of alkenes, this review focuses on significant progresses in hypervalent iodine(III)-catalyzed functionalization of alkenes as well as some asymmetric reactions employing a chiral iodoarene
In the last two decades, great progress was made in hypervalent iodine(III) catalytic systems

Summary

Introduction

Hypervalent iodine(III) reagents, named as λ3-iodanes, have been widely used in organic synthesis since the 1990s, due to their stability, low toxicity and mild reaction conditions [1,2,3,4,5,6,7,8,9,10]. When a nucleophile-tethered alkene is used, a cyclization product was obtained [34,35], stoichiometric amounts of hypervalent iodine(III) reagents were required. In 2009, Yan and co-workers reported an efficient catalytic method for the sulfonyloxylactonization of alkenoic acids (Scheme 2) [43], which employed catalytic amounts of hypervalent iodine(III) reagents and mCPBA as a stoichiometric terminal oxidant.

Results

Conclusion