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, b,g-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric g,g-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 p-complexes are in accord with the results obtained
Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids
ARCADI, Antonio;ASCHI, MASSIMILIANO;MARINELLI, Fabio
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, b,g-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric g,g-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 p-complexes are in accord with the results obtainedPubblicazioni consigliate
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