Synthesis of Tetrasubstituted Allenes via Visible-Light-Promoted Radical 1,3-Difunctionalization of Alkynyl Diazo Compounds

Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubst...

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Bibliographic Details
Published inOrganic letters Vol. 24; no. 22; pp. 3976 - 3981
Main Authors Li, Weiyu, Zhou, Lei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 10.06.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
diazo compounds
light
nitrogen
photocatalysts
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
SPECTROSCOPY
PROPARGYL
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Summary:Herein, we described an unprecedented process for generating allenyl radicals through radical addition to alkynyl diazo compounds followed by a 1,2-radical shift with the loss of nitrogen. Using this protocol, radical 1,3-difunctionalization of alkynyl diazo compounds for the synthesis of tetrasubstituted allenes with RSO2X (X = SeR′, SR′, and I) as the radical sources was developed. The reactions were promoted by visible light without photocatalyst and any additives.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.2c01366