Rhodium(I)-catalyzed one-pot synthesis of dialkyl ketones from methanol and alkenes through directed sp3 C-H bond activation of N-methylamine.
The hydroacylation of methanol with alkenes was developed using a catalytic system consisting of Rh(I), 2-amino-4-picoline and benzoic acid; the reaction is speculated to occur by the initial N-methylation of 2-amino-4-picoline with methanol, and the subsequent dehydrogenation of the resulting N-methylamine, followed by double chelation-assisted hydroimination of alkene with the imine to give dialkyl ketones after hydrolysis.
Jo
Eun-Ae
EA
Department of Chemistry and Centre for Bioactive Molecular Hybrid, Yonsei University, Seoul, 120-749, Korea.
Lee
Ji-Hyun
JH
Jun
Chul-Ho
CH
D000475:Alkenes / Q000737:chemistry*; D019817:Benzoic Acid / Q000737:chemistry; D002384:Catalysis; D006868:Hydrolysis; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D000432:Methanol / Q000737:chemistry*; D008744:Methylamines / Q000737:chemistry*; D010847:Picolines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
D000475:Alkenes; D007659:Ketones; D008744:Methylamines; D010847:Picolines; C015672:2-amino-4-picoline; D019817:Benzoic Acid; C027451:methylamine; D012238:Rhodium; D000432:Methanol