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We report an efficient and mild approach for radical dearomatization via photoinduced palladium-catalyzed reaction of three components (i.e., furans, alcohols, and bromoalkanes). In this strategy, various functionalized spiro-heterocycles were prepared from furans in one step via cascade C-C/C-O bond formation under redox neutral conditions.
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http://dx.doi.org/10.1021/acs.orglett.3c04345 | DOI Listing |
Org Lett
July 2025
Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.
Pd-catalyzed enol-directed cascade C-H functionalization and annulation of 2-aryl-1,3-dicarbonyls have been developed using vinylcyclopropanes as a coupling partner. Utilization of an intrinsic weak chelating group, C-C/C-O bond formation, substrate scope, functional group tolerance, subsequent hydrogenolysis, and hydrogenation of products to furnish alkylated 2-aryl-1,3-dicarbonyls and late-stage product modifications are the important practical features.
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 PDFOrg Lett
May 2025
School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, P. R. China.
A three-component multi-auto-tandem reaction for the construction of site-specific tricyclic furo[3,2-]coumarins via the formation of C-C, C-O, and C-S bonds in one step from 4-hydroxycoumarins/4-hydroxy-2-pyrones, ynals, and sodium sulfinates is reported. This cascade reaction efficiently produces a variety of rare C-2-functionalized furo[3,2-]coumarins in moderate to good yields under straightforward reaction conditions. Furthermore, this protocol can be extended to a three-component coupling involving 2-hydroxy-1,4-naphthoquinone, ynals, and sodium sulfinates, yielding tricyclic naphtho[2,3-]furan-4,9-dione derivatives.
View Article and Find Full Text PDFOrg Lett
March 2025
State Key Laboratory of Antiviral Drugs, Pingyuan Laboratory, School of Chemistry and Chemical Engineering, School of Environment, Henan Normal University, Xinxiang, Henan 453007, China.
Cascade annulation reactions can assemble structurally intricate polycyclic molecules from simple starting materials with enhanced efficiency and minimized production of waste. Presented herein is a concise and effective synthesis of benzoisochromene derivatives based on a C-H activation-initiated cascade formal [4+2]/[2+4] annulation of aryl enaminone with vinyl-1,3-dioxolan-2-one. In constructing the six-membered carbocycle, aryl enaminone acted as the C4 synthon while vinyl-1,3-dioxolan-2-one acted as the C2 synthon.
View Article and Find Full Text PDFJ Org Chem
December 2024
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China.
A cascade cyclization reaction comprising two halogenation reactions and a Michael addition was developed for the synthesis of chromeno[2,3-]pyrrole-3-ones . Additionally, another cascade cyclization reaction, which involves a halogenation reaction followed by two intramolecular Michael additions, was established for the synthesis of chromeno[2,3-]pyrrole-2-ones . Both types of compounds were synthesized from -hydroxyphenyl enaminones and 2-halo--alkyloxyacetamides through a process that facilitated the intramolecular formation of C-C, C-O, and C-N bonds to effectively establish two fused rings in a single operation.
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