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“Walking” of the CC π Bond over Long Distances in Pd‐Catalyzed Reactions of 2,3‐Allenoic Acids with ω‐1‐Alkenyl Halides
Author(s) -
Ma Shengming,
Yu Zhanqian
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.200250562
Subject(s) - halide , catalysis , chemistry , palladium , medicinal chemistry , polymer chemistry , organic chemistry
Taking the bond for a walk: An ω‐1‐alkenyl group was introduced at the β position of butenolides by the Pd II ‐catalyzed coupling/cyclization of 2,3‐allenoic acids with ω‐1‐alkenyl halides (see scheme). The active Pd II catalyst was regenerated through the combination of cyclic oxypalladation–carbopalladation with repeated dehydropalladation/hydropalladation–dehalopalladation.