Litcius/Paper detail

Photoalkylation/-arylation of <i>ortho</i>-Diketones with Unactivated Organic Halides

Xiao-Yu Wang, Yongqin He, Yi Zhou, Lin Lu, Xian‐Rong Song, Zhao‐Zhao Zhou, Wan‐Fa Tian, Qiang Xiao

2023Organic Letters28 citationsDOI

Abstract

A new method for conducting a reductive alkylation/arylation of 1,2-diketones using visible light and unactivated organic halides is presented in this article. This technique does not require a photocatalyst and employs Et 3 N, a tertiary amine, as a promoter. This amine aids in generating a ketyl radical and an α-aminoalkyl radical, which engages in a C–X bond activation via a halogen atom transfer process (XAT). This approach’s success hinges on utilizing Et 3 N as the promoter. This article’s mild and straightforward protocol allows for significantly expanding organic halide substrates, including primary, secondary, and aromatic organic halides and various functional groups.

Topics & Concepts

ChemistryHalideAmine gas treatingCombinatorial chemistryHalogenKetylAlkylationOrganic synthesisPhotochemistryTertiary amineMedicinal chemistryCatalysisOrganic chemistryRadicalAlkylRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesFluorine in Organic Chemistry