Improved functional group compatibility in the palladium-catalyzed synthesis of aryl amines.
[reaction: see text] The use of Pd2dba3 with bulky, electron-rich ligands 1 or 2 and LiN(TMS)2 as the base for the coupling of amines with aryl halides containing hydroxyl, amide, or enolizable keto groups is described. This protocol expands the utility of palladium-catalyzed C-N bond formation by allowing for the use of aryl halides containing these functional groups, obviating the need for protecting group manipulations.
Harris
Michele C
MC
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Huang
Xiaohua
X
Buchwald
Stephen L
SL
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000737:chemistry; D010165:Palladium / Q000737:chemistry
D000588:Amines; D006841:Hydrocarbons, Aromatic; D006846:Hydrocarbons, Halogenated; D010165:Palladium