Visible-Light Mediated Energy Transfer Enables the Synthesis of β-Lactams via Intramolecular Hydrogen Atom Transfer

Abstract

The synthesis of 2-azetidinones (β-lactams) from simple acrylamide starting materials by visible-light mediated energy transfer catalysis is reported. The reaction features a C(sp3 )-H functionalization via a variation of the Norrish-Yang photocyclization involving a carbon-to-carbon 1,5-hydrogen atom transfer (supported by deuterium labelling and DFT calculations) and can be used for the construction of a diverse range of β-lactam products.

Metadata

Item Type:	Article
Authors/Creators:	Oddy, Meghan J Kusza, Daniel A Epton, Ryan G Lynam, Jason M https://orcid.org/0000-0003-0103-9479 Unsworth, William P https://orcid.org/0000-0002-9169-5156 Petersen, Wade F
Copyright, Publisher and Additional Information:	© 2022 Wiley-VCH GmbH.
Dates:	Published: 18 November 2022 Published (online): 26 October 2022 Accepted: 7 October 2022
Institution:	The University of York
Academic Units:	The University of York > Faculty of Sciences (York) > Chemistry (York)
Funding Information:	Funder Grant number THE ROYAL SOCIETY FCG\R1\201007
Depositing User:	Pure (York)
Date Deposited:	20 Oct 2022 08:20
Last Modified:	16 Oct 2024 18:48
Published Version:	https://doi.org/10.1002/anie.202213086
Status:	Published
Refereed:	Yes
Identification Number:	10.1002/anie.202213086
Open Archives Initiative ID (OAI ID):	oai:eprints.whiterose.ac.uk:192357

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Visible-Light Mediated Energy Transfer Enables the Synthesis of β-Lactams via Intramolecular Hydrogen Atom Transfer

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