期刊
ACS CATALYSIS
卷 9, 期 8, 页码 6987-6992出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.9b02351
关键词
carbon dioxide; carboxylation; C-F bond cleavage; selectivity; copper catalysis
资金
- National Natural Science Foundation of China [21822108, 21772129]
- 973 Project from the MOST of China [2015CB856600]
- 1000 -Youth Talents Program
- Fundamental Research Funds for the Central Universities
An effective Cu-catalyzed selective formal carboxylation of C-F bonds with an atmospheric pressure of CO2 is reported. A variety of gem-difluoroalkenes, gem-difluorodienes, and alpha-trifluoro-methyl alkenes show high reactivity and selectivity for this ipso monocarboxylation. Under mild conditions, diverse important alpha-fluoroacrylic acids and alpha,alpha-difluorocarboxylates are obtained in good-to-high yields. Moreover, this operationally simple protocol features good functional group tolerance, is readily scalable, and the resulting products are readily converted into bioactive alpha-fluorinated carbonyl compounds, indicating potential application in biochemistry and drug discovery. Mechanistic studies reveal that fluorinated boronate esters might be vital intermediates in this transformation.
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