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Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling

Dupuy, Stéphanie and Zhang, Ke-Feng and Goutierre, Anne-Sophie and Baudoin, Olivier. (2016) Terminal-Selective Functionalization of Alkyl Chains by Regioconvergent Cross-Coupling. Angewandte Chemie International Edition, 55 (47). pp. 14793-14797.

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Official URL: http://edoc.unibas.ch/51789/

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Abstract

Hydrocarbons are still the most important precursors of functionalized organic molecules, which has stirred interest in the discovery of new C−H bond functionalization methods. We describe herein a new step-economical approach that enables C−C bonds to be constructed at the terminal position of linear alkanes. First, we show that secondary alkyl bromides can undergo in situ conversion into alkyl zinc bromides and regioconvergent Negishi coupling with aryl or alkenyl triflates. The use of a suitable phosphine ligand favoring Pd migration enabled the selective formation of the linear cross-coupling product. Subsequently, mixtures of secondary alkyl bromides were prepared from linear alkanes by standard bromination, and regioconvergent cross-coupling then provided access to the corresponding linear arylation product in only two steps.
Faculties and Departments:05 Faculty of Science
05 Faculty of Science > Departement Chemie
05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier and Dupuy, Stéphanie and Zhang, Ke-Feng
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article -- The final publication is available at Wiley, see Doi link
Language:English
Identification Number:
Last Modified:17 Aug 2018 11:56
Deposited On:09 Jan 2017 15:39

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