Computational Evolution Of New Catalysts For The Morita–Baylis–Hillman Reaction
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We present a de novo discovery of an efficient catalyst of the Morita–Baylis–Hillman (MBH) reaction by searching chemical space for molecules that lower the estimated barrier of the rate-determining step using a genetic algorithm (GA) starting from randomly selected tertiary amines. We identify 435 candidates, virtually all of which contain an azetidine N as the catalytically active site, which is discovered by the GA. Two molecules are selected for further study based on their predicted synthetic accessibility and have predicted rate-determining barriers that are lower than that of a known catalyst. Azetidines have not been used as catalysts for the MBH reaction. One suggested azetidine is successfully synthesized and showed an eightfold increase in activity over a commonly used catalyst. We believe this is the first experimentally verified de novo discovery of an efficient catalyst using a generative model.
Original language | English |
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Article number | e202218565 |
Journal | Angewandte Chemie |
Volume | 135 |
Issue number | 18 |
Number of pages | 8 |
ISSN | 0044-8249 |
DOIs | |
Publication status | Published - 2023 |
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