289473-83-2Relevant academic research and scientific papers
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)
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.
Drastic effect of bidentate phosphine ligands on Pd-catalyzed hydroarylation of ethyl propiolate: A simple route to arylbutadienes
Oyamada, Juzo,Kitamura, Tsugio
supporting information; scheme or table, p. 4992 - 4994 (2009/06/05)
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.
Highly selective hydroarylation of propiolic acid derivatives using a PtCl2/AgOTf catalytic system
Oyamada, Juzo,Kitamura, Tsugio
, p. 12754 - 12762 (2008/03/13)
Hydroarylation of propiolic acid derivatives with arenes in trifluoroacetic acid efficiently proceeded in the presence of PtCl2/AgOTf catalyst to give cis-cinnamic acid derivatives in good to high yields. This PtCl2/AgOTf-catalyzed r
Efficient and selective hydroarylation of propiolic acids and their esters with arenes catalyzed by a PtCl2/AgOTf system
Oyamada, Juzo,Kitamura, Tsugio
, p. 3823 - 3827 (2007/10/03)
PtCl2/AgOTf-catalyzed hydroarylation of ethyl propiolate proceeded effectively to give ethyl (2Z)-cinnamate derivatives in good to high yields, without the formation of diethyl (1E,3Z)-4-arylbuta-1,3-diene-1,3- dicarboxylates that was observed in Pd(OAc)2-catalyzed reaction. Especially, PtCl2/AgOTf-catalyzed hydroarylation of propiolic acids proceeded effectively to give (2Z)-cinnamic acids exclusively.
