Carbon−Carbon Bond Formation Using Substrate Selective Catalytic Polymers Prepared by Molecular Imprinting:  An Artificial Class II Aldolase

Abstract

A class II aldolase-mimicking synthetic polymer was prepared by the molecular imprinting of a complex between dibenzoylmethane ( 1 ) and cobalt(II) ion in a 4-vinylpyridine−styrene−divinylbenzene copolymer. This polymer was capable of selectively catalyzing the reaction of acetophenone ( 2 ) and benzaldehyde ( 3 ) to produce chalcone ( 4 ). The polymer, which demonstrated substrate selectivity and turnover, increased reaction rate eight-fold, relative to the solution reaction. The polymer was able to withstand vigourous reaction conditions, DMF and 100 °C for several weeks, while retaining most (80−95%) of its initial activity. This is the first reported example of catalytic carbon−carbon bond formation using the molecular imprinting technique.