108952-64-3

Upstream product

• 24526-73-6 (2-oxo-2H-chromen-4-yl)-acetic acid 
• 77-78-1 dimethyl sulfate 
• 90-04-0 2-methoxy-phenylamine 
• 5164-76-1 dimethyl glutaconate 
• 1059625-64-7 2-methoxybenzenediazonium 4-methylbenzenesulfonate 

Downstream Products

• 102019-08-9 3-(2-methoxy-phenyl)-3-(4-methoxy-phenyl)-glutaric acid-anhydride 
• 109471-20-7 3-(4-hydroxy-phenyl)-3-(2-methoxy-phenyl)-glutaric acid 
• 102172-48-5 3-(2-methoxy-phenyl)-3-(4-methoxy-phenyl)-glutaric acid 

Relevant academic research and scientific papers

Flexible Entry into 3-Arylpent-2-enedioic Acids via Heck-Matsuda Arylation of Dimethyl Glutaconate with Arenediazonium Tosylates

For the preparation of compound libraries of Michael acceptors with tunable reactivity toward nuclophilic selenocysteine residue of thioredoxin reductase, a range of 3-arylglutaconic acids were required. The existing methods at the time had limited scope or involved several steps. A hitherto undescribed protocol for direct palladium(II) acetate-catalyzed arylation of glutaconic acid dimethyl ester at position 3 has been developed with a diverse set of arenediazonium tosylates followed by hydrolysis. This generally good-yielding two-step sequence displayed a propensity to deliver E -configured coupling products while compounds mostly featured in the literature were predominantly Z -configured. The possibility for preparing a library of 4-arylpyridine-2,6(1 H,3 H)-diones has been exemplified.