Photoalkylation/-arylation of ortho-Diketones with Unactivated Organic Halides

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 Et3N, a tertiary amine, as a promoter. This amine aids in generating a ketyl rad...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2023-06, Vol.25 (21), p.3847-3852
Main Authors: Wang, Xiao-Yu, He, Yong-Qin, Zhou, Yi, Lu, Lin, Song, Xian-Rong, Zhou, Zhao-Zhao, Tian, Wan-Fa, Xiao, Qiang
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 Et3N, 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 Et3N 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01191