Computational Evolution Of New Catalysts For The Morita–Baylis–Hillman Reaction
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Computational Evolution Of New Catalysts For The Morita–Baylis–Hillman Reaction. / Seumer, Julius; Hansen, Jonathan Kirschner Solberg; Brøndsted Nielsen, Mogens; Jensen, Jan Halborg.
I: Angewandte Chemie, Bind 135, Nr. 18, e202218565, 2023.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Computational Evolution Of New Catalysts For The Morita–Baylis–Hillman Reaction
AU - Seumer, Julius
AU - Hansen, Jonathan Kirschner Solberg
AU - Brøndsted Nielsen, Mogens
AU - Jensen, Jan Halborg
PY - 2023
Y1 - 2023
N2 - 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.
AB - 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.
U2 - 10.1002/ange.202218565
DO - 10.1002/ange.202218565
M3 - Journal article
VL - 135
JO - Angewandte Chemie
JF - Angewandte Chemie
SN - 0044-8249
IS - 18
M1 - e202218565
ER -
ID: 337690571