Organic Chemistry Portal
Reactions > Organic Synthesis Search

Categories: C-C Bond Formation > Heteroatom-containing Molecules >

Synthesis of fluoroalkanes, perfluoralkanes and related compounds

Related:


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.