An environmentally friendly Matsuda-Heck reaction with arenediazonium tosylates has been developed for the first time. A range of alkenes was arylated in good to quantitative yields in water. The reaction is significantly accelerated when carried out under microwave heating. The arylation of haloalkylacrylates with diazonium salts has been implemented for the first time.
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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC4419561 | PMC |
http://dx.doi.org/10.3762/bjoc.11.41 | DOI Listing |
J Org Chem
July 2021
Universitaet Potsdam, Institut für Chemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
-Methylene-β-lactams were synthesized in two steps from commercially available 3-bromo-2-(bromomethyl)propionic acid and reacted with arene diazonium salts in a Heck-type arylation in the presence of catalytic amounts of Pd(OAc) under ligand-free conditions. The products, arylidene-β-lactams, were obtained in high yields as single isomers. The β-hydride elimination step of the Pd-catalyzed coupling reaction proceeds with high -regioselectivity and -stereoselectivity.
View Article and Find Full Text PDFOrg Biomol Chem
May 2021
Universitaet Potsdam, Institut fuer Chemie, Organische Synthesechemie, Karl-Liebknecht-Straße 24-25, D-14476 Potsdam-Golm, Germany.
Itaconic acid esters and hemiesters undergo Pd-catalyzed coupling reactions with arene diazonium salts in high to excellent yields. The coupling products of ortho-nitro arene diazonium salts can be converted in one or two steps to benzazepine-2-ones.
View Article and Find Full Text PDFJ Org Chem
June 2020
Key Lab of Environment and Health, School of Public Health, Xuzhou Medical University, Xuzhou 221004, Jiangsu, PR China.
A novel reaction mode and efficient ruthenium-catalyzed Matsuda-Heck-type arylation of -quinone methides (-QMs) with aryl diazonium salts has been developed for the synthesis of symmetrical or unsymmetrical δ,δ'-diaryl quinone methides (fuchsones). Aryl groups are introduced at the δ-position of -QMs via tandem olefin insertion reaction/β-H elimination processes. This reaction features advantages such as mild and green conditions, broad reactant scope, and high yields.
View Article and Find Full Text PDFJ Org Chem
November 2019
Universitaet Potsdam, Institut fuer Chemie , Karl-Liebknecht-Straße 24-25 , D-14476 Potsdam-Golm , Germany.
The methoxymethyl-protected glycal l-amicetal, synthesized de novo from l-ethyl lactate through tandem ring-closing metathesis-isomerization sequence, undergoes a highly -diastereoselective Heck-type coupling reaction with various arene diazonium salts to furnish 2,3-unsaturated aryl -glycosides in moderate to excellent yields. The products can be further functionalized, e.g.
View Article and Find Full Text PDFJ Org Chem
May 2019
Institut fuer Chemie , Universitaet Potsdam, Karl-Liebknecht-Straße 24-25 , D-14476 Potsdam-Golm , Germany.
N-Arylitaconimides, accessible from maleic anhydride, anilines, and paraformaldehyde, react with arene diazonium salts in Pd-catalyzed Matsuda-Heck arylation to the pharmacologically relevant E-configured 3-arylmethylidene pyrrolidine-2,5-diones (also known as arylmethylidene succinimides) through exo-selective β-H-elimination. The coupling proceeds at ambient temperature with the simple and easy-to-handle precatalyst Pd-II-acetate under ligand- and base-free conditions. Notable features are high isolated yields, regio- and stereoselectivities, and short reaction times.
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