A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides
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A fluorinated.pdf
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Author(s)
Sather, Aaron C.
Lee, Hong Geun
De La Rosa, Valentina Y.
Yang, Yang
Mueller, Peter
Buchwald, Stephen Leffler
Date Issued
September 2015
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Sather, Aaron C., Hong Geun Lee, Valentina Y. De La Rosa, Yang Yang, Peter Müller, and Stephen L. Buchwald. “A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides.” Journal of the American Chemical Society 137, no. 41 (October 21, 2015): 13433–13438. © 2015 American Chemical Society.
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Final published version
Abstract
A new biaryl monophosphine ligand (AlPhos, L1) allows for the room-temperature Pd-catalyzed fluorination of a variety of activated (hetero)aryl triflates. Furthermore, aryl triflates and bromides that are prone to give mixtures of regioisomeric aryl fluorides with Pd-catalysis can now be converted to the desired aryl fluorides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations, shed light on the origin of the enhanced reactivity observed with L1.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/jacs.5b09308
