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The Rh-catalyzed reactions of -pyridinyl enaminones with internal alkynes leading to the synthesis of iminopyranes via a key C-H bond activation and subsequent tautomeric O-H bond cleavage are reported. Moreover, the pyridine ring in the amino group acts as an auxiliary monodentate site for this annulation and can be easily removed by a simple hydrolysis to afford pyranones.
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http://dx.doi.org/10.1021/acs.orglett.2c00912 | DOI Listing |
Chem Commun (Camb)
August 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati-781039, India.
Rh-catalyzed C-H functionalization/annulation of arylamides with maleimides has been accomplished to furnish succinimide-tethered isoquinoline-1,3-diones. The sequential C-C/C-N bond formation, substrate scope, access to quaternary carbon and functional group tolerance are the salient features.
View Article and Find Full Text PDFAdv Sci (Weinh)
July 2025
Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
Controlling regio- and chemo-selectivity in transition-metal-catalyzed reactions involving coupling reagents with multiple reactive sites remains a significant challenge. In this study, a dual-ligand strategy is introduced to orthogonally regulate both nucleophilic and electrophilic sites in the rhodium-catalyzed sequential hydrofunctionalization of valylene. Leveraging the synergistic effects of bidentate and monodentate phosphine ligands, cyclic prenylation of 4-hydroxycoumarins is achieved with outstanding regio- and chemo-selectivity under basic conditions.
View Article and Find Full Text PDFOrg Lett
May 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Rh-catalyzed enaminone directed cascade C-H functionalization/2-fold annulation with vinylcyclopropanes has been accomplished to afford functionalized tetrahydrobenzo[]isochromen-10-ones. The sequential C-H/C-C functionalization, C-C/C-O bond formation, redox-neutral conditions, functional group tolerance, and late-stage modification of the natural products are important practical features.
View Article and Find Full Text PDFChem Commun (Camb)
May 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Rh-catalyzed weak-directing-group-facilitated sequential C-H/C-C functionalization of quinoline -oxides with cyclopropenones has been accomplished to furnish functionalized 2-quinolones. The reaction sequence involves a cascade C-C/C-N bond formation and oxygen atom transfer from water. The substrate scope, functional group tolerance and HO labelling experiment are the important practical features.
View Article and Find Full Text PDFJ Org Chem
April 2025
Guangzhou University of Chinese Medicine, Guangzhou, Guangdong 510006, China.
Herein, an efficient Rh-catalyzed C-H activation/annulation between α,β-unsaturated amides and coumarin-derived iodonium ylides has been developed, affording novel pyrano[3,2-]chromene-2,5-diones and analogues in high yields. Most products could be easily isolated by precipitation in ethanol, followed by simple filtration. Additionally, this protocol demonstrated the benefits of environmentally friendly conditions, air compatibility, good functional group compatibility, scale-up synthesis with low catalyst loading, and a recyclable Rh catalyst.
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