High turnover number and rapid, room-temperature amination of chloroarenes using saturated carbene ligands.
[equation--see text] A catalytic system for the mild amination of aryl chlorides is described. This system consists of a Pd(0) precursor and a dihydroimidazoline carbene ligand, which is generated in situ from its protonated tetrafluoroborate salt (2). Using this catalyst, aryl and heteroaryl chlorides react with secondary amines and anilines within hours at room temperature. Turnover numbers as high as 5000 are obtained at elevated temperatures for reaction of morpholine with an unactivated aryl chloride.
Stauffer
S R
SR
Department of Chemistry, Yale University, New Haven, Connecticut 06520-8107, USA.
Lee
S
S
Stambuli
J P
JP
Hauck
S I
SI
Hartwig
J F
JF
D000475:Alkenes / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D015195:Drug Design; D006838:Hydrocarbons; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D007202:Indicators and Reagents; D007700:Kinetics; D008024:Ligands; D008697:Methane / Q000031:analogs & derivatives*; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium
D000475:Alkenes; D000588:Amines; D006838:Hydrocarbons; D006843:Hydrocarbons, Chlorinated; D007202:Indicators and Reagents; D008024:Ligands; C030011:carbene; D010165:Palladium; D008697:Methane