title: Highly efficient "on water" catalyst-free nucleophilic addition reactions using difluoroenoxysilanes: dramatic fluorine effects.
abstract: A remarkable fluorine effect on "on water" reactions is reported. The CF⋅⋅⋅HO interactions between suitably fluorinated nucleophiles and the hydrogen-bond network at the phase boundary of oil droplets enable the formation of a unique microstructure to facilitate on water catalyst-free reactions, which are difficult to realize using nonfluorinated substrates. Accordingly, a highly efficient on water, catalyst-free reaction of difluoroenoxysilanes with aldehydes, activated ketones, and isatylidene malononitriles was developed, thus leading to the highly efficient synthesis of a variety of α,α-difluoro-β-hydroxy ketones and quaternary oxindoles.
authors.affiliation: Shanghai Key Laboratory of Green Chemistry and Chemical Processes, East China Normal University, 3663N, Zhongshan Road, Shanghai 200062 (China).
authors.forename: Jin-Sheng
authors.initials: JS
authors.lastname: Yu
authors.forename: Yun-Lin
authors.initials: YL
authors.lastname: Liu
authors.forename: Jing
authors.initials: J
authors.lastname: Tang
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.forename: Jian
authors.initials: J
authors.lastname: Zhou
keywords: fluorine; heterocycles; heterogeneous catalysis; synthetic methods; water chemistry