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Ligand‐Controlled α‐ and β‐Arylation of Acyclic N‐Boc Amines
Author(s) -
Millet Anthony,
Dailler David,
Larini Paolo,
Baudoin Olivier
Publication year - 2014
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.201310904
Subject(s) - transmetalation , phosphine , ligand (biochemistry) , chemistry , palladium , combinatorial chemistry , medicinal chemistry , coupling (piping) , stereochemistry , catalysis , organic chemistry , materials science , receptor , biochemistry , metallurgy
The palladium‐catalyzed ligand‐controlled arylation of α‐zincated acyclic amines, obtained by directed α‐lithiation and transmetalation, is described. Whereas P t Bu 3 gave rise to α‐arylated Boc‐protected amines, more flexible N ‐phenylazole‐based phosphine ligands induced major β‐arylation through migrative cross‐coupling.