Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 11, Pages 7864-7871Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00776
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Funding
- National Natural Science Foundation of China [51573069]
- Department of Science & Technology of Jilin Province [20170414052GH]
- Open Funds of the State Key Laboratory of Rare Earth Resource Ut i l i zation [RERU2021002]
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A metal-free method for the direct C(sp(3))-H bond alkoxylation of 3-methylfuranocoumarins with alcohols has been developed. Selectfluor was used to enable the (hetero)benzylic C-H etherification by tuning the reaction conditions. Various alcohols were found to be compatible in this transformation, yielding suitable products. Mechanistic studies suggest that the reaction may involve a double addition process of alcohols, as well as the departure of a fluoride anion and the formation of an oxonium ion.
A facile and metal-free method for the direct C(sp(3))-H bond alkoxylation of 3-methylfuranocoumarins with alcohols has been disclosed. Selectfluor enabled the (hetero)benzylic C-H etherification by tuning the reaction temperature and solvent. Various alcohols were compatible in this transformation with suitable yields. The mechanistic studies revealed that the reaction might undergo the double addition process of alcohols, as well as the departure of a fluoride anion and the formation of an oxonium ion.
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