Microcapsule Enabled Multicatalyst System

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Presentation transcript:

Microcapsule Enabled Multicatalyst System Sarah L. Poe, Muris Kobasˇlija, and D. Tyler McQuade* J. Am. Chem. Soc. 2006, 128, 15586-15587.

One-Pot Multistep Reactions advantage Be effective at reducing the waste and cost of a synthetic route decrease the number of work-ups and purifications decrease the the volume of solvent These reactions are especially useful when multiple catalysts are used so that one traps an unstable intermediate formed by the other. imitation a relatively small number of systems where the catalysts are compatible with each other.

Site–isolated catalysts = polystyrene P Patchornik, A. et al. J. Am. Chem. Soc. 1981, 103, 7620-7629.

Helms, B. et al. Angew. Chem. Int. Ed. 2005, 44,6384 – 6387.

Gelman, F. et al. J. Am. Chem. Soc. 2000, 122, 11999-12000.

Synthesis of microencapsulated poly(ethyleneimine) catalyst (0.15 g/mL PEI in 6.0 mL MeOH and 1.5 mL CHCl3 Span 85 / cyclohexane (2% v/v) 2 min Span 85 (Sorbitan trioleate) C60H108O8 PEI = 1.0 mL 2,4-tolylene diisocyanate (TDI)/ 9.0 mL cyclohexane polymerization 1 min cyclohexane (stopped) TDI = washed with hexanes

Ni(II)–bis[(R,R)-N,N’-Dibenzylcyclohexane-1,2-diamine]Br2 82 % Evans, D. A. et al. J. Am. Chem. Soc. 2005, 127, 9958-9959.

dimethyl malonate

APS : aminopropylsilica heterogeneous catalysts TEOS (Tetraethyl Orthosilicate): (C2H5O)4Si ATS (3-aminopropyl)triethoxysilane : NH2(CH2)3Si(OC2H5)3 Sartori, G. et al. J. Catal. 2004, 222, 410-418.

Michael Addition reactions