Dynamic Covalent Organocatalysts Discovered from Catalytic Systems through Rapid Deconvolution Screening |
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| Authors: | Fredrik Schaufelberger Prof Olof Ramström |
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| Affiliation: | Department of Chemistry, KTH ‐ Royal Institute of Technology, Teknikringen 30, 10044 Stockholm (Sweden) |
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| Abstract: | The first example of a bifunctional organocatalyst assembled through dynamic covalent chemistry (DCC) is described. The catalyst is based on reversible imine chemistry and can catalyze the Morita–Baylis–Hillman (MBH) reaction of enones with aldehydes or N‐tosyl imines. Furthermore, these dynamic catalysts were shown to be optimizable through a systemic screening approach, in which large mixtures of catalyst structures were generated, and the optimal catalyst could be directly identified by using dynamic deconvolution. This strategy allowed one‐pot synthesis and in situ evaluation of several potential catalysts without the need to separate, characterize, and purify each individual structure. The systems were furthermore shown to catalyze and re‐equilibrate their own formation through a previously unknown thiourea‐catalyzed transimination process. |
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| Keywords: | catalyst screening dynamic covalent chemistry organocatalysis Schiff bases transimination |
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