Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C-H Arylation.
- Yang L University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland.
- Neuburger M University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland.
- Baudoin O University of Basel, Department of Chemistry, St. Johanns-Ring 19, 4056, Basel, Switzerland.
- 2017-12-13
Published in:
- Angewandte Chemie (International ed. in English). - 2018
English
Previous enantioselective Pd0 -catalyzed C-H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimolecular mixture thereof. This study describes the development of new chiral bifunctional ligands based on a binaphthyl scaffold which incorporates both a phosphine and a carboxylic acid moiety. The optimal ligand provided high yields and enantioselectivities for a desymmetrizing C(sp2 )-H arylation leading to 5,6-dihydrophenanthridines, whereas the corresponding monofunctional ligands showed low enantioselectivities. The bifunctional system proved applicable to a range of substituted dihydrophenanthridines, and allowed the parallel kinetic resolution of racemic substrates.
- Language
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- English
- Open access status
- green
- Identifiers
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- DOI 10.1002/anie.201712061
- PMID 29231274
- Persistent URL
- https://sonar.ch/global/documents/194938
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