Palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins

Tao Pei; Xiang Wang; Ross A Widenhoefer

doi:10.1021/ja026317b

Palladium-catalyzed intramolecular oxidative alkylation of unactivated olefins

J Am Chem Soc. 2003 Jan 22;125(3):648-9. doi: 10.1021/ja026317b.

Authors

Tao Pei¹, Xiang Wang, Ross A Widenhoefer

Affiliation

¹ Duke University, P. M. Gross Chemical Laboratory, Durham, North Carolina 27708-0346, USA.

PMID: 12526661
DOI: 10.1021/ja026317b

Abstract

Reaction of 5,5-dimethyl-8-nonene-2,4-dione catalyzed by PdCl2(CH3CN)2 (5 mol %) in the presence of CuCl2 (2.5 equiv) at room temperature for 3 h formed 2-acetyl-3,6,6-trimethyl-2-cyclohexenone in 96% isolated yield. Palladium-catalyzed intramolecular oxidative alkylation tolerated a range of substitution and was applicable to the synthesis of spirobicyclic compounds and to the cyclization of zeta-alkenyl beta-keto esters.