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An Exclusively trans ‐Selective Chlorocarbamoylation of Alkynes Enabled by a Palladium/Phosphaadamantane Catalyst
Author(s) -
Le Christine M.,
Hou Xiao,
Sperger Theresa,
Schoenebeck Franziska,
Lautens Mark
Publication year - 2015
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.201507883
Subject(s) - palladium , catalysis , phosphine , chemistry , alkyne , intramolecular force , reactivity (psychology) , methylene , selectivity , combinatorial chemistry , medicinal chemistry , organic chemistry , medicine , alternative medicine , pathology
Pharmaceutically relevant methylene oxindoles are synthesized by a palladium(0)‐catalyzed intramolecular chlorocarbamoylation reaction of alkynes. A relatively underexplored class of caged phosphine ligands is uniquely suited for this transformation, enabling high levels of reactivity and exquisite trans selectivity. This report entails the first transition‐metal‐catalyzed atom‐economic addition of a carbamoyl chloride across an alkyne.