Exploration of new catalytic methodologies for heterocyclic synthesis and C-C Bond Formation.

Abstract

Amino boronate based bifiinctional molecules have the potential to be powerful catalysts. Herein, a number of approaches to the bifimctional benzimidazole catalyst 1 are described, and the synthesis of a number of analogues are explored. Investigations into the potential of 2-(2-boronobenzene)- 2N-n-butylbenzimidazole sodium hydroxide salt 1 as a catalyst for a number of synthetic transformations, including an aza-version of the Baeyer-Villiger reaction (Equation 1), are described The 2-(2-boronobenzene)-N-n-butylbenzimidazole sodium hydroxide salt 1 is shown to be active in the aldol condensation reaction (Equation 2)， Knoevenagel reaction, and evidence for the promotion of the Michael reaction by 1 is presented. The mechanism by which the aldol condensation reaction is promoted by 1 is explored through kinetic studies.