Synlett 2016; 27(20): 2761-2773
DOI: 10.1055/s-0036-1589409
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© Georg Thieme Verlag Stuttgart · New York

Benziodoxol(on)e Reagents as Tools in Organic Synthesis: The Background behind the Discovery at the Laboratory of Catalysis and Organic Synthesis

Jerome Waser*
Laboratory of Catalysis and Organic Synthesis, École Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland   Email: jerome.waser@epfl.ch
› Author Affiliations
Further Information

Publication History

Received: 15 August 2016

Accepted after revision: 10 October 2016

Publication Date:
27 October 2016 (eFirst)

Abstract

In this review, a personal account of our work in the field of hypervalent iodine reagents is presented. Pioneering experiments, which led to the discovery of the exceptional reactivity of EthynylBenziodoXol(on)e (EBX) reagents as electrophilic alkyne synthons is first discussed, including the alkynylation of ketoesters, olefins and heterocycles. Our further work involving EBX reagents in domino reactions and the alkynylation of thiols, as well as the use of benziodoxole reagents for azidation reactions is then described. Finally, the most recent results involving radicals and carbenes as reaction partners for EBX reagents and their first use in chemical biology are presented. The purpose of this review is not to give an extensive overview of our results, but to show the ‘true story’ beyond the discovery by presenting the most important pioneering experiments. Failed attempts and near misses are also briefly discussed.

1 Introduction

2 First Uses of EBX Reagents

3 Discovering New Reactions with Benziodoxole Reagents

4 New Partners for EBX Reagents

5 Going Beyond Synthetic Organic Chemistry

6 Conclusion

 
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