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Palladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C-H Bonds

Melot, Romain and Zuccarello, Marco and Cavalli, Diana and Niggli, Nadja and Devereux, Michael and Bürgi, Thomas and Baudoin, Olivier. (2021) Palladium(0)-Catalyzed Enantioselective Intramolecular Arylation of Enantiotopic Secondary C-H Bonds. Angewandte Chemie International Edition. 10.1002/anie.202014605.

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Abstract

The enantioselective functionalization of nonactivated enantiotopic secondary C-H bonds is one of the greatest challenges in transition-metal-catalyzed C-H activation proceeding by an inner-sphere mechanism. Such reactions have remained elusive within the realm of Pd0 catalysis. Reported here is the unique reactivity profile of the IBiox ligand family in the Pd0-catalyzed intramolecular arylation of such nonactivated secondary C-H bonds. Chiral C2-symmetric IBiox ligands led to high enantioselectivities for a broad range of valuable indane products containing a tertiary stereocenter, as well as the arylation of secondary C-H bonds adjacent to amides. Depending on the amide substituents and upon control of reaction time, indanes containing labile tertiary stereocenters were also obtained with high enantioselectivities. Analysis of the steric maps of the IBiox ligands indicated that the level of enantioselectivity correlates with the difference between the two most occupied and the two less occupied space quadrants, and provided a blueprint for the design of even more efficient ligands.
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:1433-7851
e-ISSN:1521-3773
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
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Last Modified:23 Feb 2021 09:53
Deposited On:23 Feb 2021 09:53

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