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

ACS Omega. 2021 Sep 27;6(40):26623-26639. doi: 10.1021/acsomega.1c03991. eCollection 2021 Oct 12.

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.

PMID:34661016 | PMC:PMC8515593 | DOI:10.1021/acsomega.1c03991

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