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Oxindole Synthesis through Intramolecular Nucleophilic Addition of Vinylpalladiums to Aryl Isocyanates
Author(s) -
Kamijo Shin,
Sasaki Yuya,
Kanazawa Chikashi,
Schüßeler Thomas,
Yamamoto Yoshinori
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502252
Subject(s) - organopalladium , intramolecular force , reactivity (psychology) , nucleophile , chemistry , oxindole , catalysis , aryl , medicinal chemistry , palladium , organic chemistry , medicine , alkyl , alternative medicine , pathology
Ringing the changes for organopalladium catalysts. A new nucleophilic reactivity of organopalladium species has been revealed. The reaction between aryl isocyanates and terminal alkynes in the presence of a palladium catalyst produces oxindoles through the intramolecular vinylpalladation of isocyanates (see scheme; dppe=1,2‐bis(diphenylphosphanyl)ethane).