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The Fate of Bis( η 3 ‐allyl)palladium Complexes in the Presence of Aldehydes (or Imines) and Allylic Chlorides: Stille Coupling versus Allylation of Aldehydes (or Imines)
Author(s) -
Nakamura Hiroyuki,
Bao Ming,
Yamamoto Yoshinori
Publication year - 2001
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 - 10.1002/1521-3773(20010903)40:17<3208::aid-anie3208>3.0.co;2-u
Subject(s) - allylic rearrangement , stille reaction , palladium , chemistry , coupling (piping) , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy
The mere presence or absence of PPh 3 suffices to control the reactivity of bis( η 3 ‐allyl)palladium complexes. In the absence of PPh 3 they undergo chemoselective allylic addition to aldehydes or imines, even in the presence of allylic chlorides, whereas in the presence of PPh 3 the Stille coupling reaction takes place chemoselectively, even when aldehydes or imines are also present (see scheme).