Gallo Rafael D C, Ahmad Anees, Metzker Gustavo, Burtoloso Antonio C B
Instituto de Química de São Carlos, Universidade de São Paulo, CEP 13560-970, São Carlos, SP, Brasil.
Chemistry. 2017 Dec 1;23(67):16980-16984. doi: 10.1002/chem.201704609. Epub 2017 Nov 20.
A one-pot alkylation-halogenation of ketosulfoxonium ylides in the presence of alkyl halides is described. The method furnishes several gem-difunctionalized haloketones (an alkyl and F, Cl, Br, or I) in good yields. Replacing alkyl halides with a mixture of electrophilic halogen species and various halide anions led to gem-dihalogenated ketones containing a combination of the same or two different halogens. Kinetic isotopic effects as well as reaction kinetic experiments give insight to the mechanism of these reactions.
本文描述了在卤代烃存在下，酮亚砜叶立德的一锅法烷基化-卤化反应。该方法能以良好的产率得到几种偕二官能化卤代酮（一个烷基和氟、氯、溴或碘）。用亲电卤素物种和各种卤离子的混合物代替卤代烃，可得到含有相同或两种不同卤素组合的偕二卤代酮。动力学同位素效应以及反应动力学实验有助于深入了解这些反应的机理。
