Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 1, Pages 1231-1237Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.0c02431
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Funding
- National Natural Science Foundation of China [21861019, 21562025]
- Natural Science Foundation of Jiangxi Province [20202ACBL203006]
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A new method for the synthesis of α-trifluoromethyl ketones has been developed by cleaving the C=C double bond on tertiary enaminones to form a new C-CF3 bond, with the promotion of TBHP and ambient heating. Control experiments show that the reactions proceed via a featured free radical process, and deuterium labeling experiments indicate the involvement of water in product formation by providing hydrogen atoms.
The C=C double bond cleavage on tertiary enaminones, enabling the formation of a new C-CF3 bond, has been realized as a practical method for the synthesis of alpha-trifluoromethyl ketones with only the promotion of TBHP and ambient heating. Control experiments support that the reactions proceed via a featured free radical process. The deuterium labeling experiment employing D2O indicates that water participated in the product formation by donating the hydrogen atom for the newly generated alpha-C-H bond in the product.
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