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Tuning the Regioselectivity in the Palladium( II )‐Catalyzed Isomerization of Alkylidene Cyclopropyl Ketones: A Dramatic Salt Effect
Author(s) -
Ma Shengming,
Zhang Junliang
Publication year - 2003
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.200390073
Subject(s) - regioselectivity , isomerization , acetone , chemistry , catalysis , salt (chemistry) , medicinal chemistry , palladium , ketone , organic chemistry
Useful building blocks are formed in this [PdCl 2 (CH 3 CN) 2 ]‐catalyzed regioselective isomerization reaction of alkylidene cyclopropyl ketones, in which a dramatic salt effect was observed. In the presence of NaI, the reaction in refluxing acetone afforded furans, while 4 H ‐pyrans were formed at RT in the absence of NaI (see scheme).