Palladium-Catalyzed Intramolecular C-H Difluoroalkylation: Synthesis of Substituted 3,3-Difluoro-2-oxindoles

Author(s)
Shi, Shi-Liang; Buchwald, Stephen Leffler
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Abstract
The synthesis of 3,3-difluoro-2-oxindoles through a robust and efficient palladium-catalyzed C-H difluoroalkylation is described. This process generates a broad range of difluorooxindoles from readily prepared starting materials. The use of BrettPhos as the ligand was crucial for high efficiency. Preliminary mechanistic studies suggest that oxidative addition is the rate-determining step for this process.
Date issued
2014-12
URI
http://hdl.handle.net/1721.1/99673
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Shi, Shi-Liang, and Stephen L. Buchwald. “Palladium-Catalyzed Intramolecular C-H Difluoroalkylation: Synthesis of Substituted 3,3-Difluoro-2-Oxindoles.” Angew. Chem. Int. Ed. 54, no. 5 (December 4, 2014): 1646–1650.
Version: Author's final manuscript
ISSN
14337851
1521-3773
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