Electrochemical C–H Alkylation of Azauracils Using <i>N</i>-(Acyloxy)phthalimides

We present an electrochemical alkylation of azauracils using <i>N</i>-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several azauracils are shown to undergo alkylation with an array of NHPI esters (1°, 2°, 3°, and sterically congested), providing the desired products in good to excellent yields. This operationally simple method is robust, scalable, and suitable for both batch and flow setups.

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Publication Details

Journal
Organic Letters
Published
2024-08-20
DOI
https://doi.org/10.1021/acs.orglett.4c02662
Citations
23
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
5.75

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Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides

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23 citations
Organic Letters
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5.75
article

Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides

Satya Prakash Panda, Siddharth Sharma, Sandip Murarka, Rupashri Dash, Kuldeep Singh Bhati
article en
23 citations

Abstract

We present an electrochemical alkylation of azauracils using <i>N</i>-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several azauracils are shown to undergo alkylation with an array of NHPI esters (1°, 2°, 3°, and sterically congested), providing the desired products in good to excellent yields. This operationally simple method is robust, scalable, and suitable for both batch and flow setups.

Organic LettersVol. 26(34)
Indian Institute of Technology Jodhpur (IN), Mohanlal Sukhadia University (IN)
Ministry of Education, India, Science and Engineering Research Board
Openalex Percentile: Top 3%
Radical Photochemical Reactions
5.75
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