Brønsted acid-catalyzed homogeneous O–H and S–H insertion reactions under metal- and ligand-free conditions
Literature Information
Publication Date
2021-01-15
DOI
10.1039/D0QO01401J
Impact Factor
5.281
Authors
Zhiqin He, Yuxing Xie, Tiantong He, Yaofeng Fu, Yang Yu
View Original
Abstract
Under metal- and ligand-free conditions, the economical and accessible CF3SO3H successfully catalyzed homogeneous O–H bond insertion reactions between hydroxyl compounds and diazo compounds. Including phenols, alcohols, water and oximes, these O–H bond insertion reactions are very general and functional-group tolerant. Here, we first report the O–H bond insertion of oximes (ketoximes and aldoximes), and their structures were characterized by X-ray crystallography. Moreover, a simple and effective method for S–H insertion reactions of thiols was also developed, delivering the desired C–S bond products with good to excellent yields. It is worth noting that the efficacy of the developed methodology could be further shown by the expeditious synthesis of the PPAR agonist MBX-102 acid.
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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
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1-(Hexopyranosyloxy)-4a,5-dihydroxy-7-methyl-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-7-yl 3-phenylacrylate
CAS Number:
19210-12-9
Molecular Formula:
C24H30O11
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