Visible light-induced aerobic dioxygenation of α,β-unsaturated amides/alkenes toward selective synthesis of β-oxy alcohols using rose bengal as a photosensitizer
Literature Information
Publication Date
2021-03-02
DOI
10.1039/D1QO00149C
Impact Factor
5.281
Authors
Ming-Zhong Zhang, Jing Tian, Min Yuan, Wan-Qi Peng, Yu-Zhu Wang, Peng Wang, Long Liu, Quan Gou, Huisheng Huang, Tieqiao Chen
View Original
Abstract
The first visible light-induced dioxygenation of α,β-unsaturated amides with N-hydroxy compounds under air was developed with the use of the non-toxic organic dye rose bengal as the photoredox catalyst. This metal-free reaction is highly chemoselective, producing the corresponding β-oxy alcohols rather than the competitive cyclized products through aminooxyarylation. Other aromatic alkenes, dihydrofurans and dienes, were also applicable to this reaction. Compared with the established radical dioxygenation methods to construct β-oxy alcohols, the present photochemical protocol avoids the use of (over)stoichiometric amounts of hazardous/poisonous oxidants, transition metals and additional reducing reagents, yielding the desired dioxygenated products in a safe and eco-friendly fashion. Moreover, the practical application of this methodology is highlighted by a concise two-step synthesis of 1,4-dioxane-2-carboxamides, a framework for building Mcl-1 inhibitors.
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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
1-(3',5'-Di-O-benzoyl-2'-deoxy-2'-fluoro-b-D-arabinofuranosyl)thymine
CAS Number:
97614-47-6
Molecular Formula:
C24H21FN2O7
![4,4-Difluoro-2-methyl-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline structure](https://static.chemtradehub.com/structs/119/1194032-23-9-f426.webp "4,4-Difluoro-2-methyl-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline structure")
4,4-Difluoro-2-methyl-1-{[(2-methyl-2-propanyl)oxy]carbonyl}-L-proline
CAS Number:
1194032-23-9
Molecular Formula:
C11H17F2NO4
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