Substrate-Controlled\nElectrochemical Reaction of 2‑Alkynylbenzamides,\nInorganic Sulfites, and Alcohols

Isoindolones constitute a dominant structural class in\nsynthetic\nand medicinal chemistry. In this research, an electrochemical reaction\ninvolving 2-alkynylbenzamides, inorganic sulfites, and alcohols was\nfirst established to provide sulfonyl ester-substituted 3-hydroxyisoindolinone\nderivatives in moderate to good yields with excellent functional group\ntolerance. When bulky aryl-substituted 2-alkynylbenzamides are utilized\nas substrates, sulfonyl ester-substituted 3-alkylideneisoindolinones\ncan be selectively generated with good chemoselectivity. Alkoxysulfonyl\nradicals derived from the anodic oxidation of inorganic sulfite with\nalcohols are involved in this transformation.

Publication Details

Journal
Figshare
Published
2024-11-06
DOI
https://doi.org/10.1021/acs.joc.4c02270.s001
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
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article

Substrate-Controlled\nElectrochemical Reaction of 2‑Alkynylbenzamides,\nInorganic Sulfites, and Alcohols

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Synthesis and pharmacology of benzodiazepine derivatives
article

Substrate-Controlled\nElectrochemical Reaction of 2‑Alkynylbenzamides,\nInorganic Sulfites, and Alcohols

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Abstract

Isoindolones constitute a dominant structural class in\nsynthetic\nand medicinal chemistry. In this research, an electrochemical reaction\ninvolving 2-alkynylbenzamides, inorganic sulfites, and alcohols was\nfirst established to provide sulfonyl ester-substituted 3-hydroxyisoindolinone\nderivatives in moderate to good yields with excellent functional group\ntolerance. When bulky aryl-substituted 2-alkynylbenzamides are utilized\nas substrates, sulfonyl ester-substituted 3-alkylideneisoindolinones\ncan be selectively generated with good chemoselectivity. Alkoxysulfonyl\nradicals derived from the anodic oxidation of inorganic sulfite with\nalcohols are involved in this transformation.

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Synthesis and pharmacology of benzodiazepine derivatives
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Substrate-Controlled\nElectrochemical Reaction of 2‑Alkynylbenzamides,\nInorganic Sulfites, and Alcohols · Figshare (2024) | TGRS Research Map | TGRS