Visible-Light-Mediated Strategies for the Preparation of Oxime Ethers Derived from O-H Insertions of Oximes into Aryldiazoacetates

Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-12, Vol.86 (23), p.17528-17532
Main Authors: Stivanin, Mateus L, Duarte, Marcelo, Leão, Luiz Paulo M O, Saito, Felipe A, Jurberg, Igor D
Format: Article
Language:English
Subjects:
Ethers
Oximes
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Summary:Two visible-light-mediated O-H insertion protocols involving oximes and aryldiazoacetates leading to different products depending on the solvent employed are reported. In DCM, direct O-H insertion takes place. In THF, there is the additional incorporation of the ring-opened form of this solvent into the structure of the product. These metal-free protocols are mild and tolerant to air and moisture. The preparation of an acaricide has been developed as an example of synthetic application.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02411