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Title

Cyanovinylation of Aldehydes: Organocatalytic Multicomponent Synthesis of Conjugated Cyanomethyl Vinyl Ethers

AuthorsDelgado-Hernández, Samuel; García-Tellado, Fernando CSIC ORCID ; Tejedor, David CSIC ORCID CVN
KeywordsCyanomethyl vinyl ethers
3-(cyanomethoxy)acrylates
Multicomponent
Cyanohydrin
Cyanovinylation
Organocatalysis
Tertiary amine
N-methyl morpholine
Issue Date6-Jul-2021
PublisherMultidisciplinary Digital Publishing Institute
CitationMolecules 26(14), 4120: 1-12 (2021)
AbstractA novel organocatalytic multicomponent cyanovinylation of aldehydes was designed for the synthesis of conjugated cyanomethyl vinyl ethers. The reaction was implemented for the synthesis of a 3-substituted 3-(cyanomethoxy)acrylates, using aldehydes as substrates, acetone cyanohydrin as the cyanide anion source, and methyl propiolate as the source of the vinyl component. The multicomponent reaction is catalyzed by N-methyl morpholine (2.5 mol%) to deliver the 3-(cyanomethoxy)acrylates in excellent yields and with preponderance of the E-isomer. The multicomponent reaction manifold is highly tolerant to the structure and composition of the aldehyde (aliphatic, aromatic, heteroaromatics), and it is instrumentally simple (one batch, open atmospheres), economic (2.5 mol% catalyst, stoichiometric reagents), environmentally friendly (no toxic waste), and sustainable (easy scalability).
Publisher version (URL)https://doi.org/10.3390/molecules26144120
URIhttp://hdl.handle.net/10261/245440
DOIhttp://dx.doi.org/10.3390/molecules26144120
E-ISSN1420-3049
Appears in Collections:(IPNA) Artículos
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