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A Fluorinated Ligand Enables Room-Temperature and Regioselective Pd-Catalyzed Fluorination of Aryl Triflates and Bromides

Aaron C. Sather, Hong Geun Lee, Valentina Y. De La Rosa, Yang Yang, Peter Müller and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email: sbuchwalmit.edu

A. C. Sather, H. G. Lee, V. Y. De La Rosa, Y. Yang, P. Müller, S. L. Buchwald, J. Am. Chem. Soc., 2015, 137, 13433-13438.

DOI: 10.1021/jacs.5b09308 (free Supporting Information)


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Abstract

A new biaryl monophosphine ligand enables a room-temperature Pd-catalyzed fluorination of various activated (hetero)aryl triflates and bromides with high regioselectivity. Analysis of the solid-state structures of several Pd(II) complexes, as well as density functional theory (DFT) calculations help to explain the enhanced reactivity.

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Key Words

Fluorination


ID: J48-Y2015