On November 2, 2016, Le, Christine M.; Sperger, Theresa; Fu, Rui; Hou, Xiao; Lim, Yong Hwan; Schoenebeck, Franziska; Lautens, Mark published an article.Reference of 2-((4-Methoxyphenyl)ethynyl)aniline The title of the article was Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides. And the article contained the following:
In the presence of PdCl2(PhCN)2 in toluene, arylalkynylphenylcarbamoyl chlorides such as I underwent regio- and stereoselective intramol. cross-coupling to yield chloromethyleneoxindoles such as II. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, formed products in >95:5 Z:E selectivity in nearly all cases and is readily scalable. Product isomerization studies and calculations of the transition state structures and energies for pathways leading to product regioisomers and diastereomers were used to study the mechanism of the reaction. The calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. I underwent stereoselective substitution and Suzuki cross-coupling reactions. The structures of a (phenylchloromethylene)oxindole, a chlorophenylquinolinone byproduct, and the substitution product of II with benzylthiol were determined by X-ray crystallog. The experimental process involved the reaction of 2-((4-Methoxyphenyl)ethynyl)aniline(cas: 157869-15-3).Reference of 2-((4-Methoxyphenyl)ethynyl)aniline
The Article related to chloromethylene oxindole regioselective diastereoselective preparation, palladium catalyst regioselective stereoselective cyclization arylalkynyl phenylcarbamoyl chloride, intramol regioselective stereoselective cross coupling arylalkynyl phenylcarbamoyl chloride and other aspects.Reference of 2-((4-Methoxyphenyl)ethynyl)aniline
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