An efficient synthetic method for the preparation of multisubstituted furans, thiophenes, and pyrroles using ynolates was developed. This novel formal [4 + 1] annulation by C2-C3 and C3-C4 bond formations includes cycloaddition, cyclization, decarboxylation, and dehydration as key steps.
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http://dx.doi.org/10.1021/ol0705200 | DOI Listing |
Chem Asian J
January 2025
Department Laboratory of Organic and Medicinal Chemistry, Meiji Pharmaceutical University, 2-522-1, Noshio, Kiyose, Tokyo, 204-8588, Japan.
The catalytic indirect reductive quenching method is facilitated by a combination of Ir(III) photoredox and sulfide dual-catalysis system. This study demonstrated a method for synthesizing multi-substituted furans by using a photoredox/sulfide dual-catalysis system. This method enables the synthesis of various furan derivatives, including spirofurans and phthalans.
View Article and Find Full Text PDFJ Org Chem
January 2025
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, 3491 Gaohai Road, Guiyang 550014, P. R. China.
A copper-catalyzed regioselective annulation reaction, conducted without ligands or oxidants, has been developed for the preparation of multisubstituted furans from the readily available starting materials, β-keto esters and propargyl acetates. This process accommodates a wide range of functional groups, resulting in furan skeletons with diverse substitution patterns. The method's potential synthetic utility is highlighted by its applicability in gram-scale preparations and late-stage modifications of natural products.
View Article and Find Full Text PDFJ Org Chem
September 2024
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, PR China.
A tandem cyclization reaction of enynones with tetrasulfides has been developed under manganese-promoted conditions, leading to the high-yield formation of various furanmethyl disulfides. This reaction is characterized by readily available starting materials, mild reaction conditions, and a broad substrate scope, making it attractive and practical. It provides a new strategy for the synthesis of disulfide-containing functionalized furans.
View Article and Find Full Text PDFOrg Lett
June 2024
State Key Laboratory of Fine Chemicals, School of Chemistry, Dalian University of Technology, Dalian 116024, China.
Multisubstituted furans occupy a pivotal position within the realms of synthetic chemistry and pharmacological science due to their distinctive chemical configurations and inherent properties. We herein introduce a tandem difunctionalization protocol of alcohols for the efficient synthesis of multisubstituted 2,3-dihydrofurans and γ-butyrolactones through the combination of photocatalysis and iron catalysis under mild conditions. Photoredox alcohol α-C(sp)-H activation and Pinner-type intramolecular cyclization are two key processes.
View Article and Find Full Text PDFChem Commun (Camb)
March 2024
School of Pharmacy, Xinxiang University, Xinxiang 453000, P. R. China.
The effective and mild [4+1] annulation of ninhydrin-derived MBH carbonates with α,β-unsaturated ketones has been developed, providing a wide range of multisubstituted furans in high yields (up to 90%) with excellent β-regioselectivities. In contrast, the polysubstituted cyclopentenes bearing dispiro-bisindanedione motifs were obtained classical [3+2] annulations by employing ninhydrin-derived MBH carbonates with 2-arylidene-1,3-indandiones under the same catalytic conditions. Furthermore, the structures of two kinds of cycloadducts were straightforwardly confirmed through X-ray diffraction analysis.
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