Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols
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Buchwald_Othogonal cu- and pd-.pdf
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1.73 MB
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Adobe PDF
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0c04460f3313044a275c40dcdef6c445
Author(s)
Maiti, Debabrata
Buchwald, Stephen Leffler
Date Issued
December 2009
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Maiti, Debabrata, and Stephen L. Buchwald. “Orthogonal Cu- and Pd-Based Catalyst Systems for the O- and N-Arylation of Aminophenols.” Journal of the American Chemical Society 131, no. 47 (December 2, 2009): 17423-17429.
Version
Author's final manuscript
Abstract
O- or N-arylated aminophenol products constitute a common structural motif in various potentially useful therapeutic agents and/or drug candidates. We have developed a complementary set of Cu- and Pd-based catalyst systems for the selective O- and N-arylation of unprotected aminophenols using aryl halides. Selective O-arylation of 3- and 4-aminophenols is achieved with copper-catalyzed methods employing picolinic acid or CyDMEDA, trans-N,N′-dimethyl-1,2-cyclohexanediamine, respectively, as the ligand. The selective formation of N-arylated products of 3- and 4-aminophenols can be obtained with BrettPhos precatalyst, a biarylmonophosphine-based palladium catalyst. 2-Aminophenol can be selectively N-arylated with CuI, although no system for the selective O-arylation could be found. Coupling partners with diverse electronic properties and a variety of functional groups can be selectively transformed under these conditions.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja9081815
