Centre in Green Chemistry and Catalysis, Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
J Am Chem Soc. 2013 May 29;135(21):7819-22. doi: 10.1021/ja402393w. Epub 2013 May 20.
Highly enantio- and diastereoenriched monofluorocyclopropanes were accessed via the Simmons-Smith fluorocyclopropanation of allylic alcohols using difluoroiodomethane and ethylzinc iodide as the substituted carbenoid precursors. The scrambling of halogens at the zinc carbenoid led to the formation of the fluorocyclopropanating agent (fluoroiodomethyl)zinc(II) fluoride. This strategy circumvented the ongoing limitation in Simmons-Smith fluorocyclopropanations relying on the use of the relatively inaccessible and expensive carbenoid precursor fluorodiiodomethane.
高对映和非对映选择性的单氟环丙烷通过烯丙醇的 Simmons-Smith 氟环丙烷化反应，使用二氟碘甲烷和碘化乙基锌作为取代卡宾前体制备得到。锌卡宾上卤素的重排导致氟环丙烷化试剂（氟碘甲基）锌（II）氟化物的形成。这种策略避免了在 Simmons-Smith 氟环丙烷化反应中依赖相对难以获得和昂贵的卡宾前体氟二碘甲烷的持续限制。
