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Synthesis of Conformationally Constrained Esters and Amines by Pd-Catalyzed α-Arylation of Hindered Substrates

Martin, Anthony and Vors, Jean-Pierre and Baudoin, Olivier. (2016) Synthesis of Conformationally Constrained Esters and Amines by Pd-Catalyzed α-Arylation of Hindered Substrates. ACS Catalysis, 6 (6). pp. 3941-3945.

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Official URL: http://edoc.unibas.ch/51788/

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Abstract

The α-arylation of sterically hindered silyl ketene acetals (SKAs) with sterically hindered aryl bromides occurs efficiently using Pd[P(t-Bu)3]2 as the optimal catalyst and ZnF2 as a promoter. Less sensitive P(t-Bu)3-based catalysts could be also employed but showed a lower activity. The reaction showed a broad scope with regard to both coupling partners, including heteroaryl bromides and cyclic SKAs. It also proved to be scalable to multigram quantities, which allowed us to further transform the ester group and to access conformationally constrained benzyl- and phenethylamines, highly sought-after building blocks for the synthesis of new agrochemicals.
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
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
e-ISSN:2155-5435
Note:Publication type according to Uni Basel Research Database: Journal article -- The final publication is available at ACS, see DOI link
Language:English
Identification Number:
Last Modified:17 Aug 2018 11:53
Deposited On:09 Jan 2017 15:35

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