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Direct Oxidative Heck Cyclizations: Intramolecular Fujiwara–Moritani Arylations for the Synthesis of Functionalized Benzofurans and Dihydrobenzofurans
Author(s) -
Zhang Haiming,
Ferreira Eric M.,
Stoltz Brian M.
Publication year - 2004
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.200461294
Subject(s) - stereocenter , dehydrogenation , intramolecular force , benzofuran , chemistry , combinatorial chemistry , palladium , oxidative phosphorylation , catalysis , organic chemistry , enantioselective synthesis , biochemistry
No extra functionalization step is required for palladium( II )‐catalyzed oxidative carbocyclizations like that shown, which provide highly substituted benzofuran and dihydrobenzofuran derivatives by net dehydrogenation. The mechanism is similar to that of Heck cyclizations. Products containing quaternary carbon stereocenters can be obtained in diastereomerically pure form.