Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 82, Issue 14, Pages 7388-7393Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01064
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Funding
- National Natural Science Foundation of China [81373277, 81402790]
- International Cooperative Program [GJHZ1622]
- Frontier Science of the Chinese Academy of Sciences [160621]
- Shanghai Commission of Science and Technology [16XD1404600, 14431905300, 14431900400]
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An unprecedented difluorination reaction was developed based on the furonaphthoquinone skeleton of natural products tanshinones and their analogues. By using Selectfluor as the fluorinating source and H2O as the hydroxyl source, a wide range of unique polycyclic alpha,alpha-difluoro beta,beta-dihydroxyl para-quinone products were achieved with yields up to 90%. The mechanistic studies revealed that the reaction might undergo tandem multiple electrophilic and nucleophilic substitutions, as well as cleavages of C-O and C-C bonds. This approach not only provides a new method to synthesis of alpha,alpha-difluoro ketones, but also affords a series of unique chemotypes for biological activity screening.
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