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.