Selectivity Control in the Palladium-catalyzed Cross-coupling of Alkyl Nucleophiles

Baudoin, Olivier. (2016) Selectivity Control in the Palladium-catalyzed Cross-coupling of Alkyl Nucleophiles. Chimia, 70 (11). pp. 768-772.

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Site-selectivity remains a major challenge in metal-catalyzed C–H bond functionalization. Most existing strategies rely on the introduction of a directing group or on the intrinsic reactivity of the substrate. In this account article, we describe the development of an alternative strategy based on the migration of an organopalladium species along an alkyl chain, wherein the phosphine ligand controls the cross-coupling site. This concept was first implemented with lithium enolates, and then extended to α-zincated alkylamines obtained by directed lithiation and transmetalation. Both the direct and the migrative cross-couplings, which are controlled by simply switching the ligand, furnish synthetically useful organic intermediates.
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:Schweizerische Chemische Gesellschaft
Note:Publication type according to Uni Basel Research Database: Journal article
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edoc DOI:
Last Modified:20 Nov 2017 07:21
Deposited On:09 Jan 2017 15:45

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