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

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(sp(3))−H functionalization via a variation of the Norrish–Yang photocyclization involving a carbon‐to‐carbon 1,5‐hydrogen a...

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Detalles Bibliográficos
Autores principales: Oddy, Meghan J., Kusza, Daniel A., Epton, Ryan G., Lynam, Jason M., Unsworth, William P., Petersen, Wade F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828223/
https://www.ncbi.nlm.nih.gov/pubmed/36205440
http://dx.doi.org/10.1002/anie.202213086
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author Oddy, Meghan J.
Kusza, Daniel A.
Epton, Ryan G.
Lynam, Jason M.
Unsworth, William P.
Petersen, Wade F.
author_facet Oddy, Meghan J.
Kusza, Daniel A.
Epton, Ryan G.
Lynam, Jason M.
Unsworth, William P.
Petersen, Wade F.
author_sort Oddy, Meghan J.
collection PubMed
description 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(sp(3))−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.
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spelling pubmed-98282232023-01-10 Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer Oddy, Meghan J. Kusza, Daniel A. Epton, Ryan G. Lynam, Jason M. Unsworth, William P. Petersen, Wade F. Angew Chem Int Ed Engl Communications 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(sp(3))−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. John Wiley and Sons Inc. 2022-10-26 2022-11-25 /pmc/articles/PMC9828223/ /pubmed/36205440 http://dx.doi.org/10.1002/anie.202213086 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Oddy, Meghan J.
Kusza, Daniel A.
Epton, Ryan G.
Lynam, Jason M.
Unsworth, William P.
Petersen, Wade F.
Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title_full Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title_fullStr Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title_full_unstemmed Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title_short Visible‐Light‐Mediated Energy Transfer Enables the Synthesis of β‐Lactams via Intramolecular Hydrogen Atom Transfer
title_sort visible‐light‐mediated energy transfer enables the synthesis of β‐lactams via intramolecular hydrogen atom transfer
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9828223/
https://www.ncbi.nlm.nih.gov/pubmed/36205440
http://dx.doi.org/10.1002/anie.202213086
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