Synthesis 2019; 51(02): 359-370
DOI: 10.1055/s-0037-1609639
short review
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Group Transfer Reactions with Hypervalent Iodine­ Reagents

Manoj K. Ghosh
a  Centre of New Technologies, University of Warsaw, Banacha 2C, 02-097 Warsaw, Poland
,
Adam A. Rajkiewicz
a  Centre of New Technologies, University of Warsaw, Banacha 2C, 02-097 Warsaw, Poland
b  Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland   Email: m.kalek@cent.uw.edu.pl
,
a  Centre of New Technologies, University of Warsaw, Banacha 2C, 02-097 Warsaw, Poland
› Author Affiliations
We acknowledge the financial support from the National Science Centre Poland (grant no. 2016/22/E/ST5/00566).
Further Information

Publication History

Received: 30 August 2018

Accepted after revision: 07 October 2018

Publication Date:
08 November 2018 (online)

Abstract

In recent years, a plethora of synthetic methods that employ hypervalent iodine compounds donating an atom or a group of atoms to an acceptor molecule have been developed. Several of these transformations utilize organocatalysis, which complements well the economic and environmental advantages offered by iodine reagents. This short review provides a systematic survey of the organocatalytic approaches that have been used to promote group transfer from hypervalent iodine species. It covers both the reactions in which an organocatalyst is applied to activate the acceptor, as well as those that exploit the organocatalytic activation of the hypervalent iodine reagent itself.

1 Introduction

2 Organocatalytic Activation of Acceptor

2.1 Amine Catalysis via Enamine and Unsaturated Iminium Formation

2.2 NHC Catalysis via Acyl Anion Equivalent and Enolate Formation

2.3 Chiral Cation Directed Catalysis and Brønsted Base Catalysis via Pairing with Stabilized Enolates

3 Organocatalytic Activation of Hypervalent Iodine Reagent

3.1 Brønsted and Lewis Acid Catalysis

3.2 Lewis Base Catalysis

3.3 Radical Reactions with Organic Promoters and Catalysts

4 Summary and Outlook

 
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