1099654-13-3Relevant academic research and scientific papers
Drastic effect of bidentate phosphine ligands on Pd-catalyzed hydroarylation of ethyl propiolate: A simple route to arylbutadienes
Oyamada, Juzo,Kitamura, Tsugio
, p. 4992 - 4994 (2008)
Palladium complexes with bidentate phosphine ligands, Pd(dppe)(OAc) 2 and Pd(dppm)(OAc)2, were found to be effective catalysts for reactions of simple arenes with ethyl propiolate, affording arylbutadiene derivatives selectively. The Royal Society of Chemistry.
Regio- and stereocontrolled reaction of arenes with ethyl propiolate catalyzed by palladium or platinum complexes with a bidentate phosphine ligand. an efficient and straightforward synthesis of (1z,3e)-1-aryl-1,3-butadienes
Oyamada, Juzo,Sakai, Mariko,Yamada, Yasunori,Kitamura, Tsugio
, p. 129 - 137 (2013/02/23)
The reaction of mesitylene with ethyl propiolate in the presence of [Pd(dppe)(OAc)2] in TFA at 30 °C for 5 h gave diethyl (2E,4Z)-4-[(2,4,6- trimethylphenyl)methylene]-2-pentenedioate selectively. Screening several bidentate phosphines ligands showed that dppe and dppm ligands are good for the arylbutadiene formation. This reaction was applied to other electron-rich arenes and found to be effective for synthesis of arylbutadienes and extended -conjugated molecules. The regio- and stereoselective addition of an arene to propiolate was confirmed by NMR and single-crystal X-ray structural analyses of the products, suggesting that the arylbutadiene formation consisted of anti addition of an arene and a metal to the triple bond of ethyl propiolate, followed by syn addition to another molecule of ethyl propiolate. Similarly, the reaction of various arenes with ethyl propiolate in the presence of [Pt(dppe)(OTf )2] catalyst gave arylbutadienes selectively. In the Pd- or Pt-catalyzed reaction of arenes with ethyl propiolate, it was found that a bidentate ligand controlled the reaction to lead the formation of arylbutadienes.
