A copper-catalyzed [3+2] annulation of -acyl ketoximes with 2-aryl malonates for the concise synthesis of 3-aryl-4-pyrrolin-2-ones has been developed. The advantage of this method lies in the use of -acyl oximes as an internal oxidant to generate the nucleophilic enamines and electrophilic -quinone methides concurrently. The subsequent nucleophilic addition undergoes selectively on the α-C of malonates.
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http://dx.doi.org/10.1039/d3cc00367a | DOI Listing |
Chem Sci
January 2025
Department of Chemistry, Indian Institute of Technology Hauz Khas Delhi New Delhi 110016 India
The direct transformation of methane into C oxygenates such as acetic acid selectively using molecular oxygen (O) is a significant challenge due to the chemical inertness of methane, the difficulty of methane C-H bond activation/C-C bond coupling and the thermodynamically favored over-oxidation. In this study, we have successfully developed a porous aluminium metal-organic framework (MOF)-supported single-site mono-copper(ii) hydroxyl catalyst [MIL-53(Al)-Cu(OH)], which is efficient in directly oxidizing methane to acetic acid in water at 175 °C with a remarkable selectivity using only O. This heterogeneous catalyst achieved an exceptional acetic acid productivity of 11 796 mmol mol h in 9.
View Article and Find Full Text PDFJ Org Chem
January 2025
Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Dual photoredox and copper-catalyzed remote asymmetric C(sp)-H alkylation of hydroxamic acid derivatives with glycine derivatives via a 1,5-hydrogen transfer (1,5-HAT) process has been realized. The reaction was characterized by redox-neutral and mild conditions, good yields, excellent enantioselectivity, and broad substrate scope. This protocol provides a straightforward and efficient strategy to prepare highly valuable enantioenriched noncanonical α-amino acids.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Nankai University, College of Chemistry, 94 Weijin Rd., 300071, Tianjin, CHINA.
Reliable methods for rapidly constructing C(sp3)-rich three-dimensional polycycles are in high demand for organic synthesis and medicinal chemistry. Although there are various mature systems for synthesizing five- or six-membered polycycles, a catalytic platform for accessing diverse cycloheptanoid-containing polycyclic scaffolds is lacking. Herein, we describe a method for copper-catalyzed intramolecular 2-aminoallyl cation-diene (4 + 3) cycloaddition reactions.
View Article and Find Full Text PDFJ Org Chem
January 2025
Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Ji'nan 250117, China.
Herein, we report a Cu-DTBP-catalyzed [3 + 2] cycloaddition reaction between 1-(2-oxo-2-phenylethyl)--indole-3-aldehyde and arylalkene, using DMF as the solvent. Under relatively mild reaction conditions, a series of indole compounds were synthesized in moderate yields (up to 73%). This protocol features good functional group tolerance and high atom economy.
View Article and Find Full Text PDFInt J Mol Sci
December 2024
Materials Research Institute, Universidad Nacional Autónoma de México, Mexico City 04510, Mexico.
Since its conceptualization, click chemistry in all its variants has proven to be a superior synthesis protocol, compared to conventional methods, for forming new covalent bonds under mild conditions, orthogonally, and with high yields. If a term like reactive resilience could be established, click reactions would be good examples, as they perform better under increasingly challenging conditions. Particularly, highly hindered couplings that perform poorly with conventional chemistry protocols-such as those used to conjugate biomacromolecules (e.
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