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Photoredox Neutral Decarboxylative Hydroxyalkylations of Heteroarenes with α-Keto Acids

Xiaochen Ji, Yang Zhong-lin, Xinzhuang Wu, Guo‐Jun Deng, Huawen Huang

2022The Journal of Organic Chemistry24 citationsDOI

Abstract

Photoredox neutral decarboxylative hydroxyalkylations of heteroarenes with α-keto acids under mild conditions are described. Stable and readily available α-keto acids were employed as hydroxyalkylating reagents with only CO2 released as the byproduct. A range of aromatic and aliphatic α-keto acids were successfully converted into hydroxyalkylated products with various heteroarenes. This transformation proceeded through a decarboxylation/Minisci addition/SCS sequence, generating a variety of valuable hydroxyalkylated heteroarenes.

Topics & Concepts

DecarboxylationReagentChemistryTransformation (genetics)Organic chemistryCombinatorial chemistryCatalysisBiochemistryGeneRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry
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