Nonorthogonal Cascade Catalysis in Multicompartment Micelles

Chemistry. 2023 Aug 1;29(43):e202301231. doi: 10.1002/chem.202301231. Epub 2023 Jun 21.

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.

Keywords: acid-base nonorthogonal cascade catalysis; bottlebrush block copolymer; multicompartment micelles; site-isolation; supported catalysis.