1610605-45-2Relevant academic research and scientific papers
Ligand-controlled α- And β-arylation of acyclic N-boc amines
Millet, Anthony,Dailler, David,Larini, Paolo,Baudoin, Olivier
, p. 2678 - 2682 (2014/03/21)
The palladium-catalyzed ligand-controlled arylation of α-zincated acyclic amines, obtained by directed α-lithiation and transmetalation, is described. Whereas PtBu3 gave rise to α-arylated Boc-protected amines, more flexible N-phenylazole-based phosphine ligands induced major β-arylation through migrative cross-coupling. All manner of control: The arylation of α-zincated acyclic Boc-protected amines was selectively performed at the α- or β-position in a ligand-controlled manner. α-Arylation occurs by direct reductive elimination of the α-palladated intermediate whereas β-arylation involves palladium migration along the alkyl chain. Boc=tert-butoxycarbonyl.
