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Selective Azidooxygenation of Alkenes Enabled by Photo-induced Radical Transfer Using Aryl-λ³-azidoiodane Species.

ABSTRACT: The photolytic radical-induced vicinal azidooxygenation of synthetically important and diverse functionalized substrates including unactivated alkenes is reported. The photoredox-catalyst/additive-free protocol enables intermolecular oxyazidation by simultaneously incorporating two new functionalities; C-O and C-N across the C=C double bond in a selective manner. Mechanistic investigations reveal the intermediacy of the azidyl radical facilitated via the photolysis of λ³-azidoiodane species and cascade proceeding to generate an active carbon-centered radical. The late-stage transformations of azido- and oxy-moieties were amply highlighted by assembling high-value drug analogs and bioactive skeletons.

SUBMITTER: Gurawa A

PROVIDER: S-EPMC8515593 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Selective Azidooxygenation of Alkenes Enabled by Photo-induced Radical Transfer Using Aryl-λ3-azidoiodane Species.

Gurawa Aakanksha A Kumar Manoj M Kashyap Sudhir S

ACS omega 20210927 40

The photolytic radical-induced vicinal azidooxygenation of synthetically important and diverse functionalized substrates including unactivated alkenes is reported. The photoredox-catalyst/additive-free protocol enables intermolecular oxyazidation by simultaneously incorporating two new functionalities; C-O and C-N across the C=C double bond in a selective manner. Mechanistic investigations reveal the intermediacy of the azidyl radical facilitated via the photolysis of ...[more]

PMID: 34661016

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