Ligand-controlled α- And β-arylation of acyclic N-boc amines
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.
Potassium Boc-protected secondary aminomethyltrifluoroborates: Synthesis and Suzuki-Miyaura cross-coupling reactions
Seven potassium Boc-protected secondary aminomethyltrifluoroborates were prepared in a standardized two-step process. The Suzuki-Miyaura cross-coupling reaction was studied with this new class of nucleophiles, and a large variety of aryl and hetaryl chlorides provided the desired products in good to excellent yields, thereby allowing easy access to secondary aminomethyl substructures.
Molander, Gary A.,Shin, Inji
p. 4458 - 4461
(2012/10/30)
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