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...

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Published inOrganic letters Vol. 25; no. 21; pp. 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 Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.06.2023
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACTIVATION
BARBIER REACTION
HALOGEN-ATOM-TRANSFER
COUPLING REACTION
BENZYLATION
CARBONYL-COMPOUNDS
AMINOALKYL RADICALS
PHOTO-ALLYLATION
ALDEHYDES
PHOTOCHEMICAL REDUCTIONS
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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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01191