82791-83-1

Upstream product

• 14271-83-1 4-methoxybenzoyl cyanide 
• 536-74-3 phenylacetylene 

Downstream Products

• 80816-53-1 5-Amino-2-(4-methoxy-phenyl)-4-phenyl-furan-3-carbonitrile 
• 1261378-94-2 (2R,3S)-2-(4-methoxybenzoyl)-3-phenyloxirane-2-carbonitrile 
• 1445582-73-9 tert-butyl 2-((3S,4R,5S)-4-cyano-4-(4-methoxybenzoyl)-5-phenyltetrahydrothiophen-3-yl)acetate 

Relevant academic research and scientific papers

Palladium-Catalyzed Acylcyanation of Terminal Arylacetylenes. Synthesis of 1,3-Diaryl-3-cyano-2-propen-1-ones and Tetrasubstituted Furans

(Z)-1,3-Diaryl-3-cyano-2-propen-1-ones ((Z)-1) are prepared from arenecarbonyl cyanide and terminal arylacetylene in the presence of Pd(OAc)2-PPh3 (1 mol amt. to Pd)-0.5dppb (1,4-bis(diphenylphosphino)butane) (0.5 mol amt. to Pd). The reaction proceeded via the formation of acetylenic ketone 3, followed by the palladium-catalyzed addition of HCN, and isomerization of the resulting (E)-1 to (Z)-1. Oxidative addition of arenecarbonyl cyanide to zero-valent palladium metal has been observed by admixture of 4-MeOC6H4COCN to Pd2(dba)3 · CHCl3-PPh3-0.5dppb oxide (dppb oxide = Ph2P(O)(CH2)4P(O)Ph2). The resulting Pd(4-MeOC6H4CO)(CN)(PPh3)(ligand) afforded (Z)-1c by reaction with phenylacetylene. Thus, the role of two kinds of phosphine, PPh3 and dppb, suggests that the former acts as a ligand and the latter works as a reductant of Pd(II). The product (Z)-1 can be photoisomerized to (E)-1 under room light in CDCl3. The product (Z)-1 was obtained by a four-component coupling reaction of 4-iodotoluene, phenylacetylene, KCN, and carbon monoxide. A new synthesis of tetrasubstituted furans is also mentioned.

Acylcyanation of Terminal Acetylenes: Palladium-Catalyzed Addition of Aryloyl Cyanides to Arylacetylenes

Two different electron-withdrawing carbon substituents (aryloyl group and nitrile group) were introduced into terminal arylacetylenes by a new method, palladium-catalyzed intermolecular acylcyanation of the acetylenic bonds.