108685-94-5

Upstream product

• 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 
• 100-52-7 benzaldehyde 
• 31021-02-0 2-phenylmethylenecyclohexan-1-one 
• 124-41-4 sodium methylate 

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.

A Michael Addition-Induced Favorskii Rearrangement

Reaction of 6-chloro-2-vinylidenecyclohexanone with sodium methoxide gave methyl 2-vinylidene-1-cyclopentanecarboxylate and methyl trans-2-(1-methoxy-alkyl)-1-cyclopentanecarboxylate along with 6-methoxy-2-vinylidenecyclohexanone via a Michael addition-induced Favorskii rearrangement.