TEMPO as Hydrogen\nAtom Transfer Catalyst in Enhancing\nIminyl Radical Cyclization of <i>O</i>‑Acetyl Oxime\ntoward Phenanthridines and Isoquinolines

Herein, we present a strategy for\npromoting the cyclization\nof <i>ortho</i>-aryl or <i>ortho</i> alkenyl arylketone\noxime ethers C–N bonds using TEMPO as a direct hydrogen atom\ntransfer (HAT) catalyst. The reaction employs a green solvent and\nrequires no introduction of metal additives. It only needs catalytic\namount of TEMPO to drive the reaction. Gram-scale reaction yields\nthe corresponding products with satisfactory yields, providing a novel\nand efficient method for the synthesis of phenanthridine and isoquinoline\nderivatives.

Publication Details

Journal
Figshare
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.joc.4c01353.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

TEMPO as Hydrogen\nAtom Transfer Catalyst in Enhancing\nIminyl Radical Cyclization of O‑Acetyl Oxime\ntoward Phenanthridines and Isoquinolines

Figshare
Radical Photochemical Reactions
article

TEMPO as Hydrogen\nAtom Transfer Catalyst in Enhancing\nIminyl Radical Cyclization of O‑Acetyl Oxime\ntoward Phenanthridines and Isoquinolines

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Abstract

Herein, we present a strategy for\npromoting the cyclization\nof <i>ortho</i>-aryl or <i>ortho</i> alkenyl arylketone\noxime ethers C–N bonds using TEMPO as a direct hydrogen atom\ntransfer (HAT) catalyst. The reaction employs a green solvent and\nrequires no introduction of metal additives. It only needs catalytic\namount of TEMPO to drive the reaction. Gram-scale reaction yields\nthe corresponding products with satisfactory yields, providing a novel\nand efficient method for the synthesis of phenanthridine and isoquinoline\nderivatives.

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Radical Photochemical Reactions
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TEMPO as Hydrogen\nAtom Transfer Catalyst in Enhancing\nIminyl Radical Cyclization of <i>O</i>‑Acetyl Oxime\ntoward Phenanthridines and Isoquinolines · Figshare (2024) | TGRS Research Map | TGRS