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Design of Chiral NHC-Carboxylates as Potential Ligands for Pd-Catalyzed Enantioselective C-H Activation

Niggli, Nadja E. and Baudoin, Olivier. (2021) Design of Chiral NHC-Carboxylates as Potential Ligands for Pd-Catalyzed Enantioselective C-H Activation. Helvetica Chimica Acta, 104. e2100015.

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Abstract

Despite numerous efforts, the synthesis of scalemic carbo- and heterocycles through Pd0-catalyzed C(sp3)-H activation employing chiral ancillary ligands or chiral bases is still limited. Inspired by the recently reported outstanding performance of IBiox-type NHC ligands and bifunctional ligands in similar transformations, a new class of bifunctional NHC-ligands bearing a pendant carboxylate group was designed. A library of 10 imidazolium-carboxylic acids was obtained in five to six steps from enantiopure L-tert-leucinol. In addition, four well-defined Pd(DMBPA)-NHC palladacycles were synthesized in good to excellent yields from the corresponding imidazolium precursors. These complexes were tested in a prototypical C(sp3)-H arylation reaction, and the most active one afforded the indoline product in low yield but significant enantioselectivity. These new bifunctional NHCs could find broader applications in catalytic enantioselective transformations occurring under milder conditions.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Synthetische Chemie (Baudoin)
UniBasel Contributors:Baudoin, Olivier
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Wiley
ISSN:0018-019X
e-ISSN:1522-2675
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
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edoc DOI:
Last Modified:02 Mar 2021 10:26
Deposited On:02 Mar 2021 10:26

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