Synthesis of IAN-type N,N-Ligands via Dynamic Kinetic Asymmetric Buchwald-Hartwig Amination
| Autor: | Pedro Ramírez-López, José M. Lassaletta, Rosario Fernández, Javier Iglesias-Sigüenza, Abel Ros, Antonio Romero-Arenas |
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| Přispěvatelé: | Universidad de Sevilla. Departamento de Química Orgánica |
| Jazyk: | angličtina |
| Rok vydání: | 2016 |
| Předmět: |
010405 organic chemistry
Chemistry Ligand Stereochemistry Aryl Cationic polymerization General Chemistry Buchwald–Hartwig amination 010402 general chemistry 01 natural sciences Biochemistry Oxidative addition Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound Colloid and Surface Chemistry Reactivity (chemistry) Amination |
| Zdroj: | idUS. Depósito de Investigación de la Universidad de Sevilla instname Digital.CSIC. Repositorio Institucional del CSIC |
| Popis: | The 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. |
| Databáze: | OpenAIRE |
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