Preparation of β-bromodifluoromethyl-functionalized esters, nitrile and ketones via addition of dibromodifluoromethane to electron-deficient alkenes initiated by a CrCl3/Fe bimetal redox system
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 1,p. 72-73
- https://doi.org/10.1039/c39930000072
Abstract
The addition of dibromodifluoromethane to electron-deficient alkenes proceeds smoothly in the presence of a CrCl3/Fe bimetal redox system, giving various β-bromodifluoromethyl-functionalized esters, nitriles and ketones in good yields.Keywords
This publication has 12 references indexed in Scilit:
- Difluoromethylation of alkenes via borohydride reduction of 1,3-dibromo-1,1-difluoroalkanesThe Journal of Organic Chemistry, 1991
- Gem-difluoroallylation of aldehydes and ketones as a convenient route to .alpha.,.alpha.-difluorohomoallylic alcoholsThe Journal of Organic Chemistry, 1991
- Triethylborane-induced stereoselective radical addition of perfluoroalkyl iodides to acetylenesTetrahedron Letters, 1989
- Synthesis and pheromonal properties of (Z)-7,7-difluoro-8-dodecenyl acetate, a difluoro derivative of the sex pheromone of the oriental fruit mothTetrahedron Letters, 1989
- Facile synthesis of ethyl 3,3-difluoroacrylate from dibromodifluoromethane and Diels-Alder cycloaddition with furanThe Journal of Organic Chemistry, 1987
- gem-(Difluoroallyl)lithium: Preparation by lithium-halogen exchange and utilization in organosilicon and organic synthesisJournal of the American Chemical Society, 1983
- Condensation of CF2Br2, CF2BrCl and BrCF2CF2Br with enamines and ynaminesTetrahedron Letters, 1981
- The copper(I) chloride-ethanolamine catalyzed addition of polyfluorinated alkanes to olefinsTetrahedron Letters, 1966
- Free-Radical Additions Involving Fluorine Compounds. VII.1 The Addition of Perhaloalkanes to Vinyl Ethyl Ether and Vinyl 2,2,2-Trifluoroethyl EtherThe Journal of Organic Chemistry, 1964
- Free Radical Additions Involving Fluorine Compounds. I. The Addition of Dibromodifluoromethane to Hydrocarbon OlefinsJournal of the American Chemical Society, 1954