In the presence of 2-amino-2-phenylpropanoate salt ( or ) as the amine source, aromatic aldehydes underwent decarboxylative transamination under very mild conditions to produce a variety of arylmethylamines in 44-99% yields. The work has provided an efficient new method for the synthesis of primary arylmethylamines.
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http://dx.doi.org/10.1021/acs.orglett.3c01234 | DOI Listing |
Org Lett
December 2024
Department of Chemistry, Faculty of Science, Hokkaido University, Sapporo, Hokkaido 060-0810, Japan.
The photocatalytic alkene-migrative chain elongation reaction of 2-phosphinostyrenes with aldehydes under mild conditions in response to blue light was demonstrated. A broad range of aldehydes, both aliphatic and aromatic, participated in this reaction to afford alkene-phosphine oxides in a -selective manner. Mechanistic experiments suggested the formation of benzophospholene-based ylide intermediates via photocatalytic cyclization of phosphinostyrenes followed by solvent-mediated proton transfer under base-free reaction conditions.
View Article and Find Full Text PDFChemistry
December 2024
Okayama University: Okayama Daigaku, Research Institute for Interdisciplinary Science, JAPAN.
Grafting carbon-based nanomaterials (CNMs) with polyglycerol (PG) improves their application potentials in biomedicine and electronics. Although "grafting from" method offers advantages over "grafting to" one in terms of operability and versatility, little is known about the reaction process of glycidol with the surface groups onto CNMs. By using graphene oxide (GO) as a multi-functional model material, we examined the reactivity of the surface groups on GO toward glycidol molecules via a set of model reactions.
View Article and Find Full Text PDFChemistry
December 2024
Università Ca' FOscari di Venezia, Scienze Molecolari e Nanosistemi, via Torino 155, MESTRE, 30172, MESTRE, ITALY.
The supramolecular resorcinarene hexameric capsule efficiently promotes the unprecedented reaction between isocyanides and electron-deficient aromatic aldehydes leading to the formation of imines and carbon monoxide. The mechanism of the reaction was investigated via isotope labelling, kinetic analysis of the reaction, computational studies and the independent synthesis of a proposed intermediate. Control experiments indicate that the formation of the key aziridinone intermediate is limited to the cavity of the capsule.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
October 2024
Department of Inorganic Chemistry and Technology, Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia.
The crystal structure of the title organic-inorganic hybrid salt, (CHN)[CdCl], (I), has been reported with four mol-ecules in the asymmetric unit in a monoclinic cell [Vassilyeva (2021 ▸). , , 7713-7722]. While using two different aldehydes in the oxidative cyclization-condensation involving CHNH·HCl to prepare a new monovalent cation with the imidazo[1,5-]pyridinium skeleton, a new polymorph was obtained for (I) in space group 1 and a unit cell with approximately half the volume of the monoclinic form.
View Article and Find Full Text PDFJ Org Chem
December 2024
Department of Chemistry, Illinois State University, Normal, Illinois 61790-4160, United States.
Acid catalyzed condensation of -alkyltripyrranes with trialdehydes derived from 1,3-cyclopentadiene or methyl-1,3-cyclopentadiene, followed by oxidation with aqueous ferric chloride solutions, gave 23-alkyl-21-carbaporphyrin-2-carbaldehydes in 22-27% yield together with weakly aromatic oxycarbaporphyrins. The carbaporphyrins reacted with palladium(II) acetate or nickel(II) acetate to give organometallic complexes but in both cases alkyl group migration took place to generate 21-alkyl derivatives. Although this type of reactivity had been observed previously for palladium complexes, this is the first time the phenomenon has been seen in nickel(II) carbaporphyrins.
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