Phenolate anion-catalyzed direct activation of inert alkyl chlorides driven by visible light
Literature Information
Publication Date
2021-09-17
DOI
10.1039/D1QO01128F
Impact Factor
5.281
Authors
Delian Wei, Xipan Li, Lei Shen, Yuzhen Ding, Kangjiang Liang, Chengfeng Xia
View Original
Abstract
Alkyl chlorides are abundant and stable chemical feedstocks, but their chemical inertness hinders their widespread availability as reactants in synthetic chemistry. In this study, we demonstrate an efficient photochemical strategy to activate inert C(sp3)–Cl bonds catalyzed by phenolate anion photocatalysts. Mechanistic studies indicate that the cleavage of unactivated C(sp3)–Cl bonds is mediated by a direct SET process from photo-excited phenolate anions. This strategy conveniently engages a diverse range of unactivated primary, secondary, and tertiary alkyl chlorides in radical C–O bond formation, dehalogenation, and cyclization under mild conditions.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure](https://static.chemtradehub.com/structs/109/109032-22-6-7c88.webp "N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure")
N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide
CAS Number:
109032-22-6
Molecular Formula:
C13H12N2O6S
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