Electrochemical\nC–H Alkylation of Azauracils\nUsing <i>N</i>‑(Acyloxy)phthalimides

We present an electrochemical alkylation of azauracils\nusing <i>N</i>-(acyloxy)phthalimides (NHPI esters) as readily\navailable\nalkyl radical progenitors under metal- and additive-free conditions.\nSeveral azauracils are shown to undergo alkylation with an array of\nNHPI esters (1°, 2°, 3°, and sterically congested),\nproviding the desired products in good to excellent yields. This operationally\nsimple method is robust, scalable, and suitable for both batch and\nflow setups.

Publication Details

Journal
Figshare
Published
2024-08-20
DOI
https://doi.org/10.1021/acs.orglett.4c02662.s001
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Electrochemical\nC–H Alkylation of Azauracils\nUsing N‑(Acyloxy)phthalimides

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Radical Photochemical Reactions
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Electrochemical\nC–H Alkylation of Azauracils\nUsing N‑(Acyloxy)phthalimides

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Abstract

We present an electrochemical alkylation of azauracils\nusing <i>N</i>-(acyloxy)phthalimides (NHPI esters) as readily\navailable\nalkyl radical progenitors under metal- and additive-free conditions.\nSeveral azauracils are shown to undergo alkylation with an array of\nNHPI esters (1°, 2°, 3°, and sterically congested),\nproviding the desired products in good to excellent yields. This operationally\nsimple method is robust, scalable, and suitable for both batch and\nflow setups.

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Radical Photochemical Reactions
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Electrochemical\nC–H Alkylation of Azauracils\nUsing <i>N</i>‑(Acyloxy)phthalimides · Figshare (2024) | TGRS Research Map | TGRS