Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trifluoromethylation
Synthesis of α-trifluoromethyl carboxylic acids, esters and amides
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Recent Literature
An electrophilic trifluoromethylation of ketene silyl acetals by hypervalent
iodine reagents proceeds under very mild conditions in the presence of a
catalytic amount of trimethylsilyl bis(trifluoromethanesulfonyl)imide. The
reaction provides a direct access to various secondary, tertiary, and quaternary
α-trifluoromethyl esters and lactones in high yield.
D. Katayev, V. Matoušek, R. Koller, A. Togni, Org. Lett.,
2015,
17, 5898-5901.
A N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of α-chloro
aldehydes provides valuable α-trifluoromethyl ester derivatives in good yields.
The unique combination of an electrophilic trifluoromethylation reagent with NHC
catalysis was the key for the functionalization of a broad range of substrate.
An enantioselective version of this reaction afforded products in moderate
yields with good ee values.
F. Gelat, A. Patra, X. Pannecoucke, A. T. Biju, T. Poisson, T. Besset, Org. Lett.,
2018, 20, 3897-3901.
In an external fluorine anion-free direct deoxyhydrotrifluoromethylation of
α-keto esters with Ph3P+CF2CO2-,
water promotes the dissociation of the CF2 group to form a CF3
moiety. The reaction provides α-trifluoromethyl esters with broad substrate
scope and high functional group compatibility.
Y. Zheng, Y. Jia, Y. Yuan, Z.-X. Jiang, Z. Yang, J. Org. Chem., 2020, 85,
10913-10923.