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Photoinduced Decarboxylative Phosphorothiolation of<i>N</i>-Hydroxyphthalimide Esters

Yu Guo, Ying Luo, Shiqiang Mu, Jian Xu, Qiuling Song

2021Organic Letters55 citationsDOI

Abstract

A visible-light-induced protocol for the synthesis of phosphorothioates is developed by employing the Ir-catalyzed decarboxylative phosphorothiolation of N-hydroxyphthalimide esters. This novel synthesis method utilizes carboxylic acids as raw material, which is stable, cheap, and commercially available. Scope studies show that this reaction has good compatibility of functional groups. Notably, both the synthesis of steric hindrance phosphorothioates and the later modification of some bioactive compounds are successfully achieved.

Topics & Concepts

ChemistrySteric effectsCatalysisCombinatorial chemistryReaction conditionsOrganic chemistryCompatibility (geochemistry)Functional groupChemical engineeringPolymerEngineeringSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
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