Issue 24, 2022

A redox-enabled strategy for intramolecular hydroamination

Abstract

Metal- or acid-catalyzed intramolecular hydroamination and Cope-type intramolecular hydroamination, a distinct concerted approach using hydroxylamines, typically suffer from significant synthetic limitations. Herein we report a process for intramolecular hydroamination that uses a redox-enabled strategy relying on efficient in situ generation of hydroxylamines by oxidation, followed by Cope-type hydroamination, then reduction of the resulting pyrrolidine N-oxide. The steps are performed sequentially in a single pot, no catalyst is required, the conditions are mild, the process is highly functional group tolerant, and no chromatography is generally required for isolation. A robustness screen and a gram-scale example further support the practicality of this approach.

Graphical abstract: A redox-enabled strategy for intramolecular hydroamination

Supplementary files

Article information

Article type
Edge Article
Submitted
24 Jan 2022
Accepted
27 May 2022
First published
30 May 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2022,13, 7264-7268

A redox-enabled strategy for intramolecular hydroamination

M. A. Allen, H. M. Ly, G. F. O'Keefe and A. M. Beauchemin, Chem. Sci., 2022, 13, 7264 DOI: 10.1039/D2SC00481J

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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