Amidation of saturated C-H bonds catalyzed by electron-deficient ruthenium and manganese porphyrins. A highly catalytic nitrogen atom transfer process.
Amidation of a variety of hydrocarbons with PhI=NTs catalyzed by ruthenium and manganese meso-tetrakis(pentafluorophenyl)porphyrins 1 and 2 afforded N-substituted amides in up to 92% yields with good to excellent substrate conversions. By employing catalyst 2, exceptionally high turnovers (up to 2600) were achieved, and the amidations can be effected by directly using PhI(OAc)(2)/NH(2)R as amidating reagents; in the case of R = COCF(3) a direct amination was realized in up to 90% yield.
Yu
X Q
XQ
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong.
Huang
J S
JS
Zhou
X G
XG
Che
C M
CM
D000577:Amides / Q000378:metabolism*; D002384:Catalysis; D004583:Electrons; D008345:Manganese / Q000378:metabolism*; D008665:Metalloporphyrins / Q000737:chemistry* / Q000378:metabolism; D009584:Nitrogen / Q000378:metabolism*; D012428:Ruthenium / Q000378:metabolism*
D000577:Amides; D008665:Metalloporphyrins; D008345:Manganese; D012428:Ruthenium; D009584:Nitrogen