Nonorthogonal Cascade Catalysis in Multicompartment Micelles
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Published on: June 8, 2016
Eman Ahmed1, Jinwon Cho2, Seung Soon Jang2
1Molecular Design Institute, Department of Chemistry, New York University, 100 Washington Square East, New York, NY, 10003, USA.
Abstract:
Multicompartment micelles (MCMs) containing acid and base sites in discrete domains are prepared from poly(norbornene)-based amphiphilic bottlebrush copolymers in aqueous media. The acid and base sites are localized in different compartments of the micelle, enabling the nonorthogonal reaction sequence: deacetalization - Knoevenagel condensation - Michael addition of acetals to 2-amino chromene derivatives. Computational simulations using dissipative particle dynamics (DPD) elucidated the bottlebrush composition required to effectively site-isolate the nonorthogonal catalysts. This contribution presents MCMs as a new class of nanostructures for one-pot multistep nonorthogonal cascade catalysis, laying the groundwork for the isolation of three or more incompatible catalysts to synthesize value-added compounds in a single reaction vessel, in water.
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