INQUISUR   21779
INSTITUTO DE QUIMICA DEL SUR
Unidad Ejecutora - UE
artículos
Título:
Direct reductive amination of aldehydes using lithium-arene(cat.) as reducing system. A simple one-pot procedure for the synthesis of secondary amines
Autor/es:
NADOR, FABIANA; MOGLIE, YANINA; CIOLINO, ANDRÉS; PIERINI, ADRIANA; DORN, VIVIANA; YUS, MIGUEL; ALONSO, FRANCISCO; RADIVOY, GABRIEL
Revista:
TETRAHEDRON LETTERS
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Lugar: Amsterdam; Año: 2012 vol. 53 p. 3156 - 3160
ISSN:
0040-4039
Resumen:
A simple one-pot procedure for the direct reductive amination of
aldehydes using lithium powder and a catalytic amount of 4,4′-di-tert-butylbiphenyl
(DTBB) or a polymer supported naphthalene as reducing system is
described. The direct reductive amination of a variety of aldehydes with
primary amines was achieved simply by adding a mixture of the
corresponding carbonyl compound and the amine, over a solution of the
lithium arenide in THF at room temperature. For most of the substrates
tested the main reaction products were the secondary amines along with
variable amounts of the corresponding alcohol and/or imine products.
Theoretical DFT calculations have been applied in order to explain the
differences in reactivity observed for aromatic substrates.