Abstract
The first example of a tandem reaction involving double-bond migration in combination with telomerization is reported. Homogeneous and heterogeneous Ru catalysts were employed as isomerization catalysts, and telomerization was realized using a homogeneous Pd(0) precursor complex with a N-heterocyclic carbene (IMes) ligand. Overall conversions approaching 60% were achieved with the best selectivity to telomerization products of 91% attained at 11% conversion. Conversion was markedly higher in the presence of longer-chain alcohol (1-butanol) as the nucleophile (telogen).
Highlights
Telomerization reactions, defined as the dimerization of dienes with incorporation of a nucleophile, have a major synthetic potential (Smutny, 1967; Zapf and Beller, 2002)
The first results for the conversion of a non-conjugated diene, 1,4-pentadiene, into telomerization products were obtained by a one-pot combination of the isomerization reaction in which 1,4-pentadiene was converted into its terminal conjugated isomer 1,3-pentadiene, followed by its telomerization with methanol or 1-butanol
Telomer isomer distribution was not determined at this stage as the main focus of this work is to determine the feasibility of the tandem reaction and the overall conversion to telomerization products
Summary
Telomerization reactions, defined as the dimerization of dienes with incorporation of a nucleophile, have a major synthetic potential (Smutny, 1967; Zapf and Beller, 2002). We demonstrate for the first time the feasibility of a tandem reaction of isomerization of internal linear to 1,3-conjugated dienes, followed by telomerization, leading to formation of functionalized long chain molecules, Figure 1. Both reactions are characterized by 100% atom economy [at full conversion, according to the definition (Trost, 1991)], and can be performed in environmentally acceptable solvents or solventless at mild conditions
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