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Palladium‐Catalyzed Carbocyclization of Alkynyl Ketones Proceeding through a Carbopalladation Pathway
Author(s) -
Chernyak Natalia,
Gorelsky Serge I.,
Gevorgyan Vladimir
Publication year - 2011
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.201006751
Subject(s) - alkyne , intramolecular force , dig , palladium , isomerization , chemistry , deprotonation , stereochemistry , combinatorial chemistry , catalysis , computer science , organic chemistry , world wide web , ion
Dig this : 5‐ exo ‐dig carbocyclization of 1 into 2 features intramolecular carbopalladation of alkyne with Pd enolate (see scheme). DFT calculations show that the key Pd enolate forms by deprotonation assisted byb Pd II acetate. Subsequent intramolecular alkyne carbopalladation, Z–E isomerization of the formed vinyl palladium species, and protiodepalladation leads to E ‐alkylidene indanones.