An Intermolecular Azidoheteroarylation of Simple Alkenes via Free-Radical Multicomponent Cascade Reactions

Based upon a radical polar effect, an intermolecular azidoheteroarylation of simple alkenes via a metal-free radical multicomponent cascade process was achieved. It allows a mild, rapid, and step-economic access to a broad range of azidoalkylated heteroaromatics. Given the diversity in transformatio...

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Bibliographic Details
Published inOrganic letters Vol. 19; no. 20; pp. 5649 - 5652
Main Authors Liu, Zhi, Liu, Zhong-Quan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.10.2017
Amer Chemical Soc
Subjects
alkenes
azides
chemical structure
Chemistry
Chemistry, Organic
derivatization
drugs
Physical Sciences
Science & Technology
CENTERED RADICALS
C-H ALKYLATION
SODIUM TRIFLUOROMETHANESULFINATE
CONVENIENT ACCESS
REACTION SYSTEM
PYRIDINE N-OXIDES
CATALYZED AZIDATION
BETA-KETO-ESTERS
ORGANIC AZIDES
UNACTIVATED ALKENES
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Summary:Based upon a radical polar effect, an intermolecular azidoheteroarylation of simple alkenes via a metal-free radical multicomponent cascade process was achieved. It allows a mild, rapid, and step-economic access to a broad range of azidoalkylated heteroaromatics. Given the diversity in transformations of organic azides and medicinally privileged scaffolds of heteroarenes, this strategy enables efficient synthesis and late-stage derivatization of drugs and candidates.
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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.7b02788