Synlett 2021; 32(06): 539-544
DOI: 10.1055/a-1277-8669
synpacts

Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations

Nathan R. Gembreska
,
Alexander K. Vogel
,
Elizabeth C. Ziegelmeyer
,
Eric Cheng
,
Fan Wu
,
Leo P. Roberts
,
Megan M. Vesoulis
,
Wei Li
Department of Chemistry and Biochemistry, School of Green Chemistry and Engineering, The University of Toledo, 2801 West Bancroft Street, Toledo, Ohio 43606, USA   Email: [email protected]
› Author Affiliations
Research reported in this publication was supported by the National Institute of General Medical Sciences of the National Institutes of Health (Award Number R15GM139156). The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. We thank the University of Toledo for an internal seed grant from the Summer Research Awards and Fellowship Programs.


We dedicate this work to the memory of Professor Kilian Muñiz

Abstract

Iodonium catalysis is described here to accomplish an intermolecular olefin oxyamination reaction. Urea is used as the O- and N-source to add across both activated and unactivated alkenes in a regioselective manner. Mechanistic studies confirm the presence of an iodonium intermediate.

1 Introduction

2 Hypothesis

3 Optimizations and Scope

4 Mechanistic Probes

5 Future Outlook



Publication History

Received: 15 September 2020

Accepted after revision: 02 October 2020

Publication Date:
02 October 2020 (online)

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 
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