A novel and efficient strategy for the synthesis of sterically hindered 4-amino-3-acyl-2-naphthols through a palladium-catalyzed coupling reaction involving isocyanide chemselective insertion and domino isomerization has been developed. The methodology, which is in accordance with the principle of "atom and step economy", efficiently constructs 4-amino-3-acyl-2-naphthols in moderate to good yields.
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http://dx.doi.org/10.1021/acs.joc.5b01269 | DOI Listing |
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Hyderabad, Kandi 502 284, Sangareddy District, Telangana, India.
This study demonstrates quick access to heteroatom-embodied complex fused polycyclic frameworks through a palladium-catalyzed domino process facilitated by microwave-assisted crossover annulation of -alkynylarylhalides and dihydrobenzofurans derivatives. The overall success of this process lies in the careful design of dihydrobenzofuran precursors that direct the initial palladium-mediated annulation step to proceed in a highly regioselective manner to furnish a single regioisomeric product. Notably, this one-pot method has witnessed good substrate scope and has furnished products with excellent yields.
View Article and Find Full Text PDFJ Org Chem
January 2025
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
A novel and highly efficient Pd-catalyzed approach for the synthesis of bis-heterocycles featuring both isoxazoline and methyleneindole motifs is demonstrated. The in situ formation of vinyl Pd(II) species through an alkyne-tethered carbamoyl chloride cyclization is crucial, and the innovative Pd-catalyzed carboetherification of β,γ-unsaturated oximes with vinyl Pd(II) species has been developed. This method is not only operationally straightforward but also exhibits a broad substrate scope and excellent functional group tolerance.
View Article and Find Full Text PDFChem Commun (Camb)
January 2025
Department of Chemistry, Indian Institute of Technology, Hyderabad, Kandi, Sangareddy, 502284, Telangana, India.
Herein, we present a hitherto unexplored efficient strategy for rapidly constructing structurally constrained and intriguing polycyclic frameworks with two adjacent quaternary centers. Remarkably, this becomes possible through palladium-catalyzed six-fold domino crossover annulations of simple 1,2-bis(2-bromoaryl)ethynes and 1,2-diarylethynes. Notably, this approach demonstrates the synthesis of both C-symmetric and unsymmetric polycyclic products.
View Article and Find Full Text PDFJ Org Chem
November 2024
School of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
A highly efficient palladium-catalyzed domino coupling reaction of -iodoaryl allene with sodium sulfonates under mild conditions is described. This novel method provides a practical protocol to access diverse indole- and benzofuran-containing sulfones by simultaneous construction of C(sp)-C(sp) bond and a C(sp)-S bonds in one pot. The salient features of this transformation include simple operations, broad substrate scope, and good functional group tolerance.
View Article and Find Full Text PDFJ Org Chem
September 2024
Department of Chemistry and Chemical Sciences, Central University of Jammu, Rahya-Suchani (Bagla), District-Samba, Jammu, Jammu and Kashmir 181143, India.
Palladium-catalyzed regiocontrolled intramolecular oxypalladation-initiated cascades of multifunctional internal alkyne bearing an -tosyl tether deliver functionalized benzazepine as an exclusive product via 6- pathway in 1,4-dioxane solvent and tetrahydroquinoline scaffold as a major product via the 5- pathway in the DMSO solvent. The role of the solvent in controlling the regioselectivity is still unknown which can be a major hurdle for further reaction development. Moreover, the reaction in DMSO suffered from having a mixture of products, and no exclusive formation of tetrahydroquinoline was achieved.
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