125334-63-6

Upstream product

• 108-86-1 bromobenzene 
• 1380097-23-3 (E)-methyl 1-acetyl-2-[(tributylstannyl)methylene]cyclopentanecarboxylate 
• 131190-09-5 methyl 1-(1-oxoethyl)-2-(phenylmethylidene)cyclopentanecarboxylate 
• 131190-10-8 methyl 2-acetyl-6-heptynoate 
• 1380097-36-8 methyl 2-(1-acetoxyethylidene)hept-6-ynoate 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 125334-60-3 2-Acetyl-hept-6-enoic acid methyl ester 
• 105-45-3 acetoacetic acid methyl ester 
• 28151-82-8 2-Benzyl-1-methoxycarbonyl-cyclopentane 
• 75-36-5 acetyl chloride 
• 1119-51-3 bromopentene 
• 125334-61-4 2-Benzyl-1,1-di-(methoxycarbonyl)-cyclopentane 

Relevant academic research and scientific papers

Mild and Functional Group Tolerant Method for Tandem Palladium-Catalyzed Carbocyclization-Coupling of ?-Acetylenic β-Ketoesters with Aryl Bromides and Chlorides

We report a new protocol for the annulative difunctionalization of acetylenes via tandem carbocyclization-coupling of ?-acetylenic β-ketoesters with aryl and heteroaryl bromides and chlorides catalyzed by the palladium species derived from an air- and moisture-stable palladacyclic precatalyst. In the tandem process, the palladium complex combines appropriate carbophilic Lewis acidity and redox activity to catalyze two mechanistically distinct reactions - nucleophilic addition of the enolate to unactivated alkyne, followed by C-C coupling. We found that a broad range of electronically varied aryl and heteroaryl bromides and chlorides underwent this reaction with various ?-acetylenic β-ketoesters, providing corresponding substituted vinylidenecyclopentanes in high yield with excellent functional group tolerance.

NEW PALLADIUM MEDIATED CYCLOPENTANATION OF ALKANES BEARING A δ NUCLEOPHILIC SUBSTITUENT

A ?-alkylpalladium intermediate generated by carbopalladation of a double bond can be intramolecularly trapped by a β-diester or a β-keto ester enolate if a cyclopentane ring is formed.Otherwise, normal β-elimination is observed.