Formation of ArF from LPdAr(F): catalytic conversion of aryl triflates to aryl fluorides.
Despite increasing pharmaceutical importance, fluorinated aromatic organic molecules remain difficult to synthesize. Present methods require either harsh reaction conditions or highly specialized reagents, making the preparation of complex fluoroarenes challenging. Thus, the development of general methods for their preparation that overcome the limitations of those techniques currently in use is of great interest. We have prepared [LPd(II)Ar(F)] complexes, where L is a biaryl monophosphine ligand and Ar is an aryl group, and identified conditions under which reductive elimination occurs to form an Ar-F bond. On the basis of these results, we have developed a catalytic process that converts aryl bromides and aryl triflates into the corresponding fluorinated arenes by using simple fluoride salts. We expect this method to allow the introduction of fluorine atoms into advanced, highly functionalized intermediates.
Watson
Donald A
DA
Department of Chemistry, Massachusetts Institute of Technology (MIT), Cambridge, MA 02139, USA.
Su
Mingjuan
M
Teverovskiy
Georgiy
G
Zhang
Yong
Y
García-Fortanet
Jorge
J
Kinzel
Tom
T
Buchwald
Stephen L
SL
D002384:Catalysis; D055598:Chemical Phenomena; D003287:Contrast Media; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D007536:Isomerism; D008024:Ligands; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D049268:Positron-Emission Tomography
D003287:Contrast Media; D005462:Fluorine Radioisotopes; D006845:Hydrocarbons, Fluorinated; D008024:Ligands; D008698:Mesylates; D005461:Fluorine; D010165:Palladium; D005459:Fluorides
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