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Highly Efficient “On Water” Catalyst‐Free Nucleophilic Addition Reactions Using Difluoroenoxysilanes: Dramatic Fluorine Effects
Author(s) -
Yu JinSheng,
Liu YunLin,
Tang Jing,
Wang Xin,
Zhou Jian
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201404432
Subject(s) - catalysis , fluorine , nucleophile , chemistry , nucleophilic addition , hydrogen bond , organic chemistry , combinatorial chemistry , molecule
A remarkable fluorine effect on “on water” reactions is reported. The CF⋅⋅⋅HO 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.