Rhodium- and Palladium-Catalyzed Hydroarylation of Propargylic Amines with Arylboronic Acids
 
Antonio Arcadi 1, Massimiliano Aschi 1, Marco Chiarini 2, Giovanni Ferrara 1, Fabio Marinelli 1 *
1Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università dell'Aquila, via Vetoio, I-67100 L'Aquila, Italy, Fax: (+39)-086-243-3752; phone: (+39)-347-983-6282
2Dipartimento di Scienze degli Alimenti, Università degli Studi di Teramo, via Carlo R. Lerici 1, I-64023 Mosciano Sant'Angelo (TE), Italy
 
email: Fabio Marinelli (fabio.marinelli@univaq.it)

*Correspondence to Fabio Marinelli, 1Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università dell'Aquila, via Vetoio, I-67100 L'Aquila, Italy, Fax: (+39)-086-243-3752; phone: (+39)-347-983-6282

Funded by:
 Ministero dellUniversità e della Ricerca Scientifica e Tecnologica, Rome
 University of LAquila

FULL TEXT
KEYWORDS
alkynes • arylboronic acids • hydroarylation • palladium • propargylic amines • rhodium

 

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, ,-diarylallylamines were isolated in good yields. By contrast, the formation of the regiosomeric ,-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 -complexes are in accord with the results obtained.

Received: 6 November 2009