Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2-Isoxazolines via a Formal C(sp3)−H Functionalization

Jonathan Da Luz; Farhaan Dobah; James A. Rossi-Ashton; Richard J. Payne; William P. Unsworth; Wade F. Petersen

doi:10.1002/ejoc.202401369

Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ²-Isoxazolines via a Formal C(sp³)−H Functionalization

Jonathan Da Luz, Farhaan Dobah, James A. Rossi-Ashton, Richard J. Payne, William P. Unsworth, Wade F. Petersen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

The discovery of a dehydrogenative photoredox catalyzed formal C(sp³)−H intramolecular cyclization of indolyl-oximes to generate indolyl Δ²-isoxazolines is reported. In contrast to the current state-of-the-art, the reaction avoids the use of super stoichiometric chemical oxidants and high reaction temperatures and is proposed to operate via two sequential single electron oxidation events.

Original language	English
Article number	e202401369
Number of pages	5
Journal	European Journal of Organic Chemistry
Early online date	7 Jan 2025
DOIs	https://doi.org/10.1002/ejoc.202401369
Publication status	E-pub ahead of print - 7 Jan 2025

Bibliographical note

Publisher Copyright:
© 2024 The Author(s). European Journal of Organic Chemistry published by Wiley-VCH GmbH.

Keywords

C−H functionalization
Indoles
Isoxazolines
Oximes
Photoredox catalysis

Access to Document

10.1002/ejoc.202401369Licence: CC BY

Eur J Org Chem - 2024 - Da Luz - Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl 2‐Isoxazolines via a Formal C
© 2024 The Author(s).
Final published version, 3.92 MBLicence: CC BY

Cite this

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title = "Dehydrogenative Photoredox Catalyzed Synthesis of Indolyl Δ2-Isoxazolines via a Formal C(sp3)−H Functionalization",

abstract = "The discovery of a dehydrogenative photoredox catalyzed formal C(sp3)−H intramolecular cyclization of indolyl-oximes to generate indolyl Δ2-isoxazolines is reported. In contrast to the current state-of-the-art, the reaction avoids the use of super stoichiometric chemical oxidants and high reaction temperatures and is proposed to operate via two sequential single electron oxidation events.",

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AU - Rossi-Ashton, James A.

AU - Payne, Richard J.

AU - Unsworth, William P.

AU - Petersen, Wade F.

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KW - Isoxazolines

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KW - Photoredox catalysis

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