sp3 C-H bond arylation directed by amidine protecting group: alpha-arylation of pyrrolidines and piperidines.
A new ruthenium-catalyzed direct sp3 C-H to C-C bond transformation is disclosed. Specifically, a method for the alpha-arylation of cyclic amines, containing either permanent (pyridine, pyrimidine) or removable (amidine) directing groups, is described. This cross-coupling reaction involves heating amine substrates with arylboronate ester at 150 degrees C in a ketone solvent with a catalytic amount of ruthenium carbonyl [Ru3(CO)12]. Arylboronate esters containing either electron-withdrawing or electron-donating substituents could be efficiently coupled. Heteroarene boronates were also effective donors.
Pastine
Stefan J
SJ
Department of Chemistry, Columbia University, 3000 Broadway, New York, New York 10027, USA.
Gribkov
Denis V
DV
Sames
Dalibor
D
D000578:Amidines / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006859:Hydrogen / Q000737:chemistry*; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry*; D013237:Stereoisomerism
D000578:Amidines; D006841:Hydrocarbons, Aromatic; D010880:Piperidines; D011759:Pyrrolidines; D002244:Carbon; D006859:Hydrogen