65936-11-0Relevant articles and documents
Pronounced rate enhancements in condensation reactions attributed to the fluorous tag in modified Mukaiyama reagents
Matsugi, Masato,Nakamura, Shuichi,Kunda, Yoko,Sugiyama, Yuya,Shioiri, Takayuki
, p. 133 - 135 (2010)
The observed rate enhancement for the condensation reaction between 2-phenyl benzoic acid and isopropanol mediated by fluorous Mukaiyama reagents is described. It is shown that Mukaiyama reagents bearing a fluorous tag increase the reaction rate considerably when compared to their non-fluorous tagged counterpart. Furthermore, it is observed that the longer the fluorous chain, the higher the activity of the Mukaiyama reagent.
A fluorous Mukaiyama coupling reagent for a concise condensation reaction: Utility of medium-fluorous strategy
Sugiyama, Yuya,Kurata, Yuki,Kunda, Yoko,Miyazaki, Atsushi,Matsui, Junko,Nakamura, Shuichi,Hamamoto, Hiromi,Shioiri, Takayuki,Matsugi, Masato
scheme or table, p. 3885 - 3892 (2012/07/02)
The entire study of condensation reactions using various fluorous Mukaiyama reagents, including a novel medium-fluorous strategy, is described. A Mukaiyama reagent bearing a medium-fluorous content tag, between 40 and 60% fluorine by weight, was prepared and examined in ester and amide-forming condensation reactions. At the end of the reactions, the fluorous pyridone by-product was effectively separated from non-fluorous components by increasing the water content of the crude reaction mixture and subsequent filtration of the precipitate. It is also shown that Mukaiyama reagents bearing a fluorous tag increase the reaction rate considerably when compared to their non-fluorous tagged counterpart. Interestingly, it was observed that the longer the fluorous chain, the higher the activity of the Mukaiyama reagent.