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ID 59915
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Author
Iwai, Kenta Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
Ono, Masakazu Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
Nanjo, Yoshiko Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University
Ema, Tadashi Division of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University ORCID Kaken ID publons researchmap
Abstract
Attempts were made to minimize the amounts of catalyst and solvent in the NHC-catalyzed benzoin reactions of solid aldehydes. In some case, solid-to-solid conversions proceeded in the solvent-free NHC-catalyzed benzoin reactions. Even if a mixture of the substrate, N-heterocyclic carbene (NHC) precursor, and inorganic base was initially a powdery solid, the reaction did proceed at reaction temperature lower than the melting points of each compound. The solid mixture partially melted or became a slurry or suspension in the meantime. We call this solid/liquid mixture a semisolid state. The reaction giving an optically active product was faster than that giving a racemic mixture of the same product. Melting-point depression was observed for a series of mixtures of the substrate and product in different substrate/product ratios. Solvent-free solid-to-solid conversions were accelerated by the formation of a semisolid state resulting from the melting-point depression of the solid substrate accompanied by the product formation. In the case of solid substrates with high melting points, melting-point depression was useless, and the addition of a small amount of solvent was needed. The first total synthesis of isodarparvinol B was achieved via the NHC-catalyzed intramolecular benzoin reaction using a small amount of solvent as an additive.
Published Date
2020-04-20
Publication Title
ACS Omega
Volume
volume5
Issue
issue17
Publisher
American Chemical Society
Start Page
10207
End Page
10216
ISSN
2470-1343
Content Type
Journal Article
language
英語
OAI-PMH Set
岡山大学
Copyright Holders
© 2020 American Chemical Society
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publisher
PubMed ID
DOI
Web of Science KeyUT
Related Url
isVersionOf https://doi.org/10.1021/acsomega.0c01141
Funder Name
Japan Society for the Promotion of Science
助成番号
25288078