Categories: C-C Bond Formation > Heteroatom-containing Molecules >
Synthesis of fluoroalkanes, perfluoralkanes and related compounds
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| Synthesis of | ||||||
 Trifluoromethyl carbinols |
 Trifluoromethyl ketones |
 Triflouromethyl arenes |
Recent Literature
Intermolecular addition of perfluoroalkyl radicals on electron rich alkenes and
alkenes with electron withdrawing groups in water, mediated by silyl radicals
gives perfluoroalkyl-substituted compounds in good yields. The radical
triggering events employed consist of thermal decomposition of 1,1′-azobis(cyclohexanecarbonitrile)
(ACCN) or dioxygen initiation.
S. Barata-Vallejo, A. Postigo, J. Org. Chem., 2010,
75, 6141-6148.
The addition of (pentafluoroethyl)- and (heptafluoropropyl)lithium to Weinreb
and morpholine amides led to polyfluoro ketones in high to quantitative yields
in short reaction times. The methodology can provide inhibitors for various
lipolytic enzymes, including phospholipase A2.
C. G. Kokotos, C. Baskakis, G. Kokotos, J. Org. Chem., 2008,
73, 8623-2626.
A nucleophilic trifluoromethylation reaction of carbonyl
compounds with Ruppert’s reagent, Me3SiCF3, was efficiently
promoted by a P(t-Bu)3-DMF system. Imines were also converted to the desired
α-trifluoromethyl amines under similar reaction conditions.
S. Mizuta, N. Shibata, T. Sato, H. Fujimoto, S. Nakamura, T. Toru, Synlett,
2006, 267-270.
Alkoxide-induced nucleophilic pentafluoroethylation and trifluoromethylation
of aldehydes, ketones, and imines using pentafluoroethyl phenyl sulfone and
trifluoromethyl phenyl sulfone, respectively, have been successfully achieved.
G. K. S. Prakash, Y. Wang, R. Mogi, J. Hu, T. Mathew, G. A. Olah, Org. Lett., 2010,
12, 2932-2935.
G. K. S. Prakash, Y. Wang, R. Mogi, J. Hu, T. Mathew, G. A. Olah, Org. Lett., 2010,
12, 2932-2935.
Sodium bromodifluoroacetate (BrCF2CO2Na) is an effective
difluorocarbene source for high-yielding synthesis of gem-difluorocyclopropanes
and gem-difluorocyclopropenes under mild conditions.
K. Oshiro, Y. Morimoto, H. Amii, Synthesis, 2010,
2080-2084.
