The Institute of Organic Chemistry and Biochemistry, Czech Academy of Sciences , Flemingovo náměstí 2, 166 10 Prague 6, Czech Republic.
Laboratory of Molecular Structure Characterization, Institute of Microbiology, Academy of Sciences of the Czech Republic , Vídeňská 1083, 142 20 Prague 4, Czech Republic.
Org Lett. 2016 Nov 18;18(22):5844-5847. doi: 10.1021/acs.orglett.6b02890. Epub 2016 Oct 31.
Tetrafluoroalkyl bromides are metalated with equimolar iPrMgCl·LiCl (Turbo Grignard) to form organomagnesium compounds which are stable at low temperatures and react with various electrophiles (aldehydes, ketones, CO, cyclic sulfate and sulfamidate, N-sulfonylimines, nitrone, chlorophosphate, nonaflyl azide) to afford novel functionalized tetrafluoroethylene-containing products. Ease of operation, excellent selectivity, high nucleophilicity, and enhanced stability of the reactive species together with a broad substrate scope comprise a highly attractive nucleophilic tetrafluoroethylation protocol affording unique synthetic building blocks.
四氟烷基溴与等摩尔的异丙基氯化镁·氯化锂（Turbo Grignard）金属化，形成在低温下稳定的有机镁化合物，可与各种亲电试剂（醛、酮、CO、环状硫酸酯和磺酰胺、N-磺酰亚胺、硝酮、氯膦酸酯、九氟戊基叠氮化物）反应，得到新型功能化的含四氟乙烯的产物。操作简便、选择性好、亲核性高、反应物种稳定性增强以及底物范围广泛，构成了一种极具吸引力的亲核四氟乙基化反应方案，提供了独特的合成砌块。
