Palladium-catalyzed amination of aryl nonaflates.
The first detailed study of the palladium-catalyzed amination of aryl nonaflates is reported. Use of ligands 2-4 and 6 allows for the catalytic amination of electron-rich and -neutral aryl nonaflates with both primary and secondary amines. With use of Xantphos 5, the catalytic amination of a variety of functionalized aryl nonaflates resulted in excellent yields of anilines; even 2-carboxymethyl aryl nonaflate is effectively coupled with a primary alkylamine. Moderate yields were obtained when coupling halo-aryl nonaflates with a variety of amines, where in most cases the aryl nonaflate reacted in preference to the aryl halide. Overall, aryl nonaflates are an effective alternative to triflates in palladium-catalyzed C-N bond-forming processes due to their increased stability under the reaction conditions.
Anderson
Kevin W
KW
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Mendez-Perez
Maria
M
Priego
Julian
J
Buchwald
Stephen L
SL
D000478:Alkylation; D000586:Amination; D000588:Amines / Q000737:chemistry*; D000814:Aniline Compounds / Q000138:chemical synthesis*; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D008024:Ligands; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010636:Phenols / Q000737:chemistry
D000588:Amines; D000814:Aniline Compounds; D006841:Hydrocarbons, Aromatic; D008024:Ligands; D008698:Mesylates; D010636:Phenols; D010165:Palladium; C012077:trifluoromethanesulfonic acid