Tandem isomerization/telomerization of long chain dienes

Torrente-Murciano, Laura; Nielsen, David J; Cavell, Kingsley J; Lapkin, Alexei

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Authors

Torrente-Murciano, Laura

Nielsen, David J

Cavell, Kingsley J

Lapkin, Alexei

Publication Date

2014-06-13

Journal Title

Frontiers in Chemistry

ISSN

2296-2646

Publisher

Frontiers

Volume

Language

English

Type

Article

Metadata

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Citation

Torrente-Murciano, L., Nielsen, D. J., Cavell, K. J., & Lapkin, A. (2014). Tandem isomerization/telomerization of long chain dienes. Frontiers in Chemistry, 2 https://doi.org/10.3389/fchem.2014.00037

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).

Keywords

tandem reaction, transition metals, carbenes, C-C coupling reactions, isomerization, telomerization

Sponsorship

Financial support from Engineering and Physical Sciences Research Council (EPSRC, UK) via grant GR/S86112/01 is gratefully acknowledged.

Identifiers

External DOI: https://doi.org/10.3389/fchem.2014.00037

This record's URL: https://www.repository.cam.ac.uk/handle/1810/245399

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Attribution 2.0 UK: England & Wales

Licence URL: http://creativecommons.org/licenses/by/2.0/uk/

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Except where otherwise noted, this item's licence is described as Attribution 2.0 UK: England & Wales