753451-47-7Relevant academic research and scientific papers
Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides
Le, Christine M.,Sperger, Theresa,Fu, Rui,Hou, Xiao,Lim, Yong Hwan,Schoenebeck, Franziska,Lautens, Mark
, p. 14441 - 14448 (2016/11/13)
We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. 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. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.
Stereoselective synthesis of 3-alkylideneoxindoles via palladium-catalyzed domino reactions
Yanada, Reiko,Obika, Shingo,Inokuma, Tsubasa,Yanada, Kazuo,Yamashita, Masayuki,Ohta, Shunsaku,Takemoto, Yoshiji
, p. 6972 - 6975 (2007/10/03)
We have developed efficient catalytic methods for the stereoselective and diversity synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles and 3-alkylidene-benzofuran-2-ones via palladium-catalyzed Heck/Suzuki-Miyaura, Heck/Heck, and Hec
Stereoselective synthesis of 3-alkylideneoxindoles using tandem indium-mediated carbometallation and palladium-catalyzed cross-coupling reactions
Yanada, Reiko,Obika, Shingo,Kobayashi, Yusuke,Inokuma, Tsubasa,Oyama, Munetaka,Yanada, Kazuo,Takemoto, Yoshiji
, p. 1632 - 1642 (2007/10/03)
The first efficient methods for the stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles via radical cyclization reactions were investigated using tandem indium-mediated carbometallation and palladium-catalyzed cross-co
Stereoselective synthesis of 3-alkylideneoxindoles using tandem in-mediated carbometalation and Pd-catalyzed cross-coupling reaction
Yanada, Reiko,Obika, Shingo,Oyama, Munetaka,Takemoto, Yoshiji
, p. 2825 - 2828 (2007/10/03)
Efficient methods for stereoselective synthesis of various (E)-, (Z)-, and disubstituted 3-alkylideneoxindoles were investigated using tandem In-mediated carbometalation and ligandless Pd-catalyzed coupling reaction.
