The hydroarylation of 3-arylprop-2-yn-1-amine derivatives with arylboronic acids has been studied in the presence of rhodium or palladium catalysts. By using a rhodium-based catalytic system, β,γ-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric γ,γ-diarylallylamines was achieved by means of a palladium catalyst in the presence of acetic acid. The complementary regioselectivity displayed by these two processes is a consequence of different catalytic cycles, involving respectively carborhodation or hydropalladation of the coordinated alkyne as key steps. Calculated charge distributions in the π-complexes are in accord with the results obtained.
Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids
CHIARINI, MARCO;
2010-01-01
Abstract
The hydroarylation of 3-arylprop-2-yn-1-amine derivatives with arylboronic acids has been studied in the presence of rhodium or palladium catalysts. By using a rhodium-based catalytic system, β,γ-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric γ,γ-diarylallylamines was achieved by means of a palladium catalyst in the presence of acetic acid. The complementary regioselectivity displayed by these two processes is a consequence of different catalytic cycles, involving respectively carborhodation or hydropalladation of the coordinated alkyne as key steps. Calculated charge distributions in the π-complexes are in accord with the results obtained.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
