The Pd-catalyzed Heck-type coupling (Matsuda-Heck reaction) of electron rich arene diazonium salts with electron deficient olefins has been exploited for the synthesis of phenylpropanoid natural products. Examples described herein are the naturally occurring benzofurans methyl wutaifuranate, wutaifuranol, wutaifuranal, their 7-methoxy derivatives, and the O-prenylated natural products boropinols A and C.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/acs.joc.7b00447 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Synthesis of Benzopyran-Phenylpropanoid Hybrids via Matsuda-Heck-Arylation and Allylic Oxidation.
J Org Chem
December 2024
Universitaet Potsdam, Institut fuer Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
The synthesis of coumarin- and flavonoid-chalcone hybrids via Pd-catalyzed Heck-type coupling of arene diazonium salts and 8-allylcoumarins and -flavonoids is reported. The β-hydride elimination step proceeds with high regioselectivity if an OMOM-substituent is present at the position C7, adjacent to the allyl group. A selective allylic oxidation of the coupling products was accomplished using DDQ in the presence of silica to furnish the chalcones.
View Article and Find Full Text PDFDemonstrating Synergistic Activity of Magnetic Iron Oxide Nano Photocatalyst for C-H Activation in Heterogeneous Phase.
Chemistry
December 2024
Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, 741246, India.
This report describes a dual catalytic approach for the versatile C-H arylation of arenes under photo-excitation at room temperature. The cooperative catalysis utilizes iron oxide magnetic nanoparticles (which mostly contain FeO along with some γ-FeO) as the potential photocatalyst, which merges with the Pd-catalyzed C-H activation cycle for the reductive generation of aryl radical from aryl diazonium salt, revealing its photocatalytic activities. The method is applicable to a wide range of aryl coupling partners and different directing groups, demonstrating excellent productivity, nice co-operativity and recyclability.
View Article and Find Full Text PDFTunable and Photoactivatable Mimics of Calicheamicin γ for DNA Cleavage.
J Am Chem Soc
September 2024
Department of Chemistry, New York University, 100 Washington Square East, New York, New York 10003, United States.
Calicheamicin γ and related natural products are renowned for their potency in DNA cleavage, serving as the warheads in commercial ADCs used for treating leukemia. Their mechanism of action involves the formation of aryl radicals, which abstract hydrogen atoms from nucleic acids. However, the complex strained enediyne structure of calicheamicin γ presents significant challenges in synthesis, resulting in high production costs and limited structural and activity modularity for tuning the therapeutic window.
View Article and Find Full Text PDFCalixarene-coated gold nanorods as robust photothermal agents.
Nanoscale
October 2024
Laboratoire de Chimie Organique, Université Libre de Bruxelles (ULB), Avenue F. D. Roosevelt 50, CP160/06, B-1050 Brussels, Belgium.
Gold nanorods (AuNRs) hold considerable promise for their use in biomedical applications, notably in the context of photothermal therapy (PTT). Yet, their anisotropic nature presents a notable hurdle. Under laser irradiation, these structures are prone to deformation, leading to changes in their optical and photothermal properties over time.
View Article and Find Full Text PDFMultipodal Au-C grafting of calix[4]arene molecules on gold nanorods.
Chem Sci
August 2024
Univ Rennes, ENSCR, CNRS, ISCR (Institut des Sciences Chimiques de Rennes) - UMR 6226 F-35000 Rennes France
The interface robustness and spatial arrangement of functional molecules on metallic nanomaterials play a key part in the potential applications of functional nano-objects. The design of mechanically stable and electronically coupled attachments with the underlying metal is essential to bring specific desirable properties to the resulting hybrid materials. In this context, rigid multipodal platforms constitute a unique opportunity for the controllable grafting of functionality.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!