Catalyst discovery is a time-consuming process and simplified screening protocols are highly desirable. An ideal solution would be to synthesize several potential catalysts in the same reaction, and then identify the most catalytically active species in situ without the need for isolation, purification and characterization of the individual components. We have developed an approach to such a screening method based on dynamic covalent chemistry, in which a library of bifunctional organocatalysts for the Morita-Baylis-Hillman (MBH) reaction has been synthesized and identification of the best catalyst could be done directly from the library.The method is based on bifunctional catalyst architectures where a reversible imine bond connects the two functionalities. This design element allowed generation and deconvolution of a library of 16 MBH organocatalysts, and the optimal catalyst could be accurately predicted directly from the library. Furthermore, the libraries were shown to catalyze and re-equilibrate their own formation through H-bonding catalysis by one of the bifunctional components. These results indicate that dynamic covalent chemistry can be used to find effective organocatalysts from large libraries, even for highly challenging reaction types such as MBH reactions. 

Dynamic combinatorial organocatalysis: Discovery-oriented screening of self-correcting catalyst libraries

248th National Meeting (2014)

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