Ruthenium Catalyzed Hydrohydroxyalkylation of Isoprene with Heteroaromatic Secondary Alcohols: Isolation and Reversible Formation of the Putative Metallacycle Intermediate

by Boyoung Y. Park, T. Patrick Montgomery, Victoria J. Garza and Michael J. Krische*

Heteroaromatic secondary alcohols react with isoprene to form products of hydrohydroxyalkylation in the presence of ruthenium(0) catalysts generated from Ru₃(CO)₁₂and tricyclohexylphosphine, enabling direct conversion of secondary to tertiary alcohols in the absence of premetalated reagents or stoichiometric byproducts. The putative oxaruthenacycle intermediate has been isolated and characterized, and reversible metallacycle formation has been demonstrated.

Journal of the American Chemical Society

Publication Date (Web): October 24, 2013

DOI: 10.1021/ja4087193