Pd-catalyzed sequential C-C bond formation and cleavage: evidence for an unexpected generation of arylpalladium(II) species.

Autor: Youn SW; Department of Chemistry and Research Institute for Natural Sciences, Hanyang University, Seoul 133-791, Korea. sowony73@hanyang.ac.kr, Kim BS, Jagdale AR
Jazyk: angličtina
Zdroj: Journal of the American Chemical Society [J Am Chem Soc] 2012 Jul 18; Vol. 134 (28), pp. 11308-11. Date of Electronic Publication: 2012 Jul 05.
DOI: 10.1021/ja304616q
Abstrakt: A Pd(II)-catalyzed reaction engaging alkenyl β-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven β-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.
Databáze: MEDLINE