180585-48-2Relevant academic research and scientific papers
Palladium-Catalyzed One-Pot Four-Component Synthesis of β-Cyano-α,β-unsaturated Ketones Using Calcium Carbide as an Acetylene Source and Potassium Hexacyanoferrate(II) as an Eco-Friendly Cyanide Source
Lu, Hao,Li, Zheng
, p. 4474 - 4482 (2019)
Palladium-catalyzed one-pot four-component synthesis of β-cyano-α,β-unsaturated ketones by the reactions of aryl halides, calcium carbide, potassium hexacyanoferrate(II) and aroyl chlorides is described. The salient features of this protocol are the direct use of easy-to-handle acetylene source and eco-friendly cyanide source, wide scope of substrates with good functional group tolerance, and simple work-up procedure. (Figure presented.).
Palladium-Catalyzed Acylcyanation of Terminal Arylacetylenes. Synthesis of 1,3-Diaryl-3-cyano-2-propen-1-ones and Tetrasubstituted Furans
Nozaki, Kyoko,Sato, Naomasa,Takaya, Hidemasa
, p. 1629 - 1637 (2007/10/03)
(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.
