Squaramide-IRMOF-16 Analogue for Catalysis of Solvent-Free, Epoxide Ring-Opening Tandem and Multicomponent Reactions

Abstract

Tandem and multicomponent one-pot reactions are highly attractive because they enable synthesis of target molecules in a single reaction vessel. However, they are difficult to control, as they can lead to the formation of many undesired side-products. Herein we report the use of metal-organic framework (MOF) pores decorated with organocatalytic squaramide moieties to confine ring-opening epoxide reactions of diverse substrates. Controlled mono-addition or tandem reactions inside the pores yield 1,2-aminoalcohols or 1,2,2′-aminodialcohols, respectively, in good yields. In addition, this squaramide-functionalised MOF enables catalysis of higher-complexity multicomponent reactions such as the catalytic ring-opening of two different epoxides by a single amine to afford 1,2,2′-aminodialcohols.