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Synlett 2021; 32(06): 539-544
DOI: 10.1055/a-1277-8669
DOI: 10.1055/a-1277-8669
synpacts
Halonium Catalysis: An Underutilized and Underexplored Catalytic Concept in Olefin Functionalizations
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
Key words
iodonium catalysis - olefin oxyamination - regioselective - N-heterocycles - oxazolines - aminooxygenationPublication History
Received: 15 September 2020
Accepted after revision: 02 October 2020
Accepted Manuscript online:
02 October 2020
Article published online:
16 November 2020
© 2020. Thieme. All rights reserved
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References and Notes
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Current addresses:
For a selected recent review, see:
For selected recent examples, see:
For selected reviews on halofunctionalization and halogenation, see:
For selected examples on halocyclization processes, see:
A very interesting early example using bromine catalysis was also demonstrated by Sharpless, see:
For selected stoichiometric examples, see:
For selected reviews on olefin difunctionalizations, see:
For selected recent examples on olefin difunctionalizations, see:
For selected examples of osmium-catalyzed strategies, see:
For selected intramolecular examples based on palladium-catalysis, see:
For selected recent reviews and examples based on copper catalysis, see:
For a selected example of Ir-catalyzed strategies, see:
For selected examples based on other metal-catalyzed strategies, see:
For selected examples of metal-free strategies, see:
For selected examples of intermolecular alkene oxyamination strategies, see:
For selected reviews and examples of using directing groups in alkene difunctionalizations, see:
For other selected synthetic examples for this class of heterocycles, see:
For selected examples of regiodivergent couplings, see: