INFIQC 05475
INSTITUTO DE INVESTIGACIONES EN FISICO- QUIMICA DE CORDOBA
Unidad Ejecutora - UE
artículos
Título:
Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles
Autor/es:
SUTAR, SURAJ M.; BOROSKY, GABRIELA L.; KALKHAMBKAR, RAJESH G.; LAALI, KENNETH K.; SAVANUR, HEMANTKUMAR M.; ARIDOSS, GOPALAKRISHNAN
Revista:
TETRAHEDRON LETTERS
Editorial:
PERGAMON-ELSEVIER SCIENCE LTD
Referencias:
Año: 2020 vol. 61
ISSN:
0040-4039
Resumen:
Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in twosteps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, andemploying [BMIM(SO3H)][OTf] (neat or with [BMIM][PF6] as co-solvent) or tetramethyl guanidinium-ILs [TMG][X] (X = CF3COO, EtOSO3) as dual catalyst/solvent, followed by a Pd-catalyzed directed regioselective orthoACAH arylation of the Ritter amides with Ar-X (X = I, Cl). The feasibility to perform the two steps in sequence is also demonstrated, and potential for recycling/reuse of the ILs is also shown. Preference for [Pd] coordination to the amide carbonyl versus amide nitrogen is borne out by DFT computations.
