‘Fluorous nanoflow’ system for the Mukaiyama aldol reaction catalyzed by the lowest concentration of the lanthanide complex with bis(perfluorooctanesulfonyl)amide ponytail

Reactions and Polymerizations at the Liquid–Liquid Interface

“…Mikami and co-workers reported a dramatic increase in reactivity of Mukaiyama aldol reaction in a "fluorous nanoflow" system (nanoflow microreactor with fluorous lanthanide catalysts) (Figure 8) even at very low Lewis acid catalyst concentrations (less than 0.1 mM). 97 The reaction was complete within seconds of a biphasic contact time, whereas under vigorous stirring, it required more than 2 h and showed poor yields. A narrower width and a longer channel, thus a larger contact area, led to further improvement.…”

Continuous flow reactors: a perspective

“…32 Employing a biphasic solvent system comprising of coflowing perfluoromethylcyclohexane/toluene, Mikami et al 33 demonstrated the ability to readily recycle a Lewis acid catalyst Scheme 10 Illustration of a polymer-supported cinchonidine derivative 22 used to promote the enantioselective Michael addition in a packedbed reactor.…”

“…When looking to improve the environmental performance of a chemical process, solvents play a large role in the defining process costs and safety; consequently, the use and definition of 'green solvents' has attracted significant interest. 32 Employing a biphasic solvent system comprising of coflowing perfluoromethylcyclohexane/toluene, Mikami et al 33 demonstrated the ability to readily recycle a Lewis acid catalyst for use in the aldol reaction. As Scheme 11 illustrates, the model reaction involved the reaction of a silyl derivative 26 and aldehyde 27 (2 : 1) in the presence of scandium bis(perfluorooctanesulfonyl)amide 28 (0.06 mol%); with quantification performed offline using GC-FID analysis of the toluene phase.…”

Multiphase Organic Synthesis in Microchannel Reactors

“…To date, fluorous biphasic catalysis has attracted a great deal of attention particularly with respect to environmentally friendly chemical processes 11. The first example of fluorous biphasic catalysis in a microchannel was reported, and a dramatic increase in reactivity of Mukaiyama aldol reactions in fluorous media through a “fluorous nanoflow” system was shown 12. Even at low concentrations (<0.0001 M ) of a Lewis acid catalyst (Sc[N(SO 2 C 8 F 17 ) 2 ] 3 ) in nonpolar fluorous solvents, the reaction was complete within seconds of a biphasic contact time.…”