<i>Cine-</i> Substitution of Enolates: Enolate Dance/Coupling of Cycloalkenyl Pivalates by Nickel Catalysis

Abstract

This manuscript describes the development of the Ni/dcype-catalyzed enolate dance/coupling reaction of alkenyl pivalates with nucleophiles, resulting in cine -substitution. Pivalates derived from 1-tetralone undergo this reaction to produce C2-functionalized dihydronaphthalenes. The direct utilization of 1-tetralone is also feasible, employing Piv 2 O to generate the corresponding enol pivalate in situ . Mechanistic investigations, including stoichiometric experiments, suggest that the reaction proceeds via C–O oxidative addition, nickel 1,2-translocation, and subsequent coupling with a nucleophile.

Topics & Concepts