Open AccessSelective Azidooxygenation of Alkenes Enabled by Photo-induced Radical Transfer Using Aryl-λ3-azidoiodane Species
Author(s) -
Aakanksha Gurawa,
M. Kumar,
Sudhir Kashyap
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c03991
Subject(s) - vicinal , chemistry , intermolecular force , photoredox catalysis , photodissociation , aryl , photochemistry , radical , catalysis , combinatorial chemistry , aryl radical , cascade , organic chemistry , molecule , alkyl , photocatalysis , chromatography
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 λ 3 -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.