Chemoselective C-H bond activation: ligand and solvent free iron-catalyzed oxidative C-C cross-coupling of tertiary amines with terminal alkynes. Reaction scope and mechanism.
FeCl(2) catalyzes the oxidative C-C cross-coupling of tertiary amines with terminal alkynes into propargylamines using (t-BuO)(2) as oxidant. The reaction can be applied to aromatic and aliphatic amines and alkynes without solvent. High chemoselectivity for aminomethyl groups is due to a steric factor.
Volla
Chandra M Rao
CM
Laboratoire de glycochimie et de synthese asymetrique (LGSA), Swiss Federal Institute of Technology of Lausanne (EPFL), CH 1015 Lausanne, Switzerland.
Vogel
Pierre
P
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry*; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005296:Ferrous Compounds / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D011437:Propylamines / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D000588:Amines; D005296:Ferrous Compounds; D011437:Propylamines; C009054:propargylamine; D010293:Pargyline; C029451:ferrous chloride