Chloropalladated propargyl amine: a highly efficient phosphine-free catalyst precursor for the Heck reaction

Crestina S Consorti; Mara L Zanini; Sheila Leal; Gunter Ebeling; Jaïrton Dupont

doi:10.1021/ol027337l

Chloropalladated propargyl amine: a highly efficient phosphine-free catalyst precursor for the Heck reaction

Org Lett. 2003 Apr 3;5(7):983-6. doi: 10.1021/ol027337l.

Authors

Crestina S Consorti¹, Mara L Zanini, Sheila Leal, Gunter Ebeling, Jaïrton Dupont

Affiliation

¹ Laboratory of Molecular Catalysis, IQ UFRGS, Av. Bento Gonçalves, 9500 Porto Alegre, 91501-970 RS, Brazil.

PMID: 12659554
DOI: 10.1021/ol027337l

Abstract

[reaction: see text] The palladacycle (Pd[k(1)-C, k(1)-N-C=(C(6)H(5))C(Cl)CH(2)NMe(2)](mu-Cl))(2) 1 derived from the chloropalladation of 3-(dimethylamino)-1-phenyl-1-propyne promotes the arylation of olefins under relatively mild reaction conditions. The coupling of iodoarenes and activated bromoarenes with n-butylacrylate and styrene occurs at room temperature. Turnover numbers of up to 85 000 have been achieved with deactivated bromoarenes and up to 1000 for activated chloroarenes at higher temperatures (80-150 degrees C).