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Allylic Substitution versus Suzuki Cross‐Coupling: Capitalizing on Chemoselectivity with Bifunctional Substrates
Author(s) -
Hussain Mahmud M.,
Walsh Patrick J.
Publication year - 2010
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.200905399
Subject(s) - allylic rearrangement , chemoselectivity , substitution (logic) , chemistry , bromide , organic chemistry , medicinal chemistry , catalysis , computer science , programming language
One catalyst, two reactions—a tale of chemoselectivity : Given the choice between an allylic acetate and a vinylboronate ester, palladium preferentially reacts with the allylic acetate to give the allylic substitution product. In the presence of an aryl bromide and base, Suzuki cross‐coupling subsequently ensues to afford allylic amines (see scheme; pin=pinacol, THF=tetrahydrofuran).