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Synthesis of IAN-type N,N-Ligands via Dynamic Kinetic Asymmetric Buchwald-Hartwig Amination

AuthorsRamírez-López, Pedro; Ros, Abel ; Romero-Arenas, Antonio; Iglesias-Sigüenza, Javier; Fernández, Rosario; Lassaletta, José M.
Issue Date2016
PublisherAmerican Chemical Society
CitationJournal of the American Chemical Society 138: 12053- 12056 (2016)
AbstractThe Pd-catalyzed coupling of racemic heterobiaryl bromides, triflates, or nonaflates with aryl/alkyl primary amines using QUINAP as the ligand provides the corresponding axially chiral heterobiaryl amines with excellent yields and enantioselectivities. Reactivity and structural studies of neutral and cationic oxidative addition intermediates support a dynamic kinetic asymmetric amination mechanism based on the labilization of the stereogenic axis in the latter and suggest that coordination of the amine to the Pd center is the stereodetermining step.
Identifiersdoi: 10.1021/jacs.6b07972
issn: 1520-5126
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