Synthesis of gem‐Difluorinated Spiro‐γ‐lactam Oxindoles by Visible‐Light‐Induced Consecutive Difluoromethylative Dearomatization, Hydroxylation, and Oxidation

Described herein is a protocol for visible‐light‐induced consecutive synthesis of gem‐difluorinated spiro‐γ‐lactam oxindoles under mild conditions by means of a process involving sequential radical difluoromethylative dearomatization, hydroxylation, and oxidation. The protocol features high chemo‐ a...

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Bibliographic Details
Published in:Chemistry : a European journal 2018-08, Vol.24 (44), p.11283-11287
Main Authors: Wang, Qiang, Qu, Yi, Xia, Qing, Song, Hongjian, Song, Haibin, Liu, Yuxiu, Wang, Qingmin
Format: Article
Language:English
Subjects:
Amides
Chemistry
Functional groups
Fungicidal activity
Fungicides
Hydroxylation
nitrogen heterocycles
Oxidation
oxindoles
photocatalysis
Regioselectivity
spiro compounds
Synthesis
synthetic methods
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Summary:Described herein is a protocol for visible‐light‐induced consecutive synthesis of gem‐difluorinated spiro‐γ‐lactam oxindoles under mild conditions by means of a process involving sequential radical difluoromethylative dearomatization, hydroxylation, and oxidation. The protocol features high chemo‐ and regioselectivity, good functional group tolerance, and easy scalability. Several of the functionalized spirooxindole products showed good fungicidal activity, suggesting that they have potential agrochemical applications. The consecutive synthesis of gem‐difluorinated spiro‐γ‐lactam oxindoles was achieved by visible‐light‐induced sequential radical difluoromethylative dearomatization, hydroxylation, and oxidation. The fungicidal activity of several representative products highlights the potential utility of this reaction for agrochemical applications.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201802141