A practical synthesis of alpha-aryl methyl ketones via a transition-metal-free Meerwein arylation.
We report herein a simple, scalable, transition-metal-free approach to the synthesis of alpha-aryl methyl ketones from diazonium tetrafluoroborate salts under mild conditions. This methodology uses easily accessible and nontoxic starting material and was applied to the multi-kilogram-scale preparation of 1-(3-bromo-4-methylphenyl)propan-2-one.
Molinaro
Carmela
C
Department of Process Research, Merck Frosst Centre for Therapeutic Research, 16711 Autoroute Transcanadienne, Kirkland, Québec, Canada H9H 3L1. carmela_molinaro@merck.com
Mowat
Jeffrey
J
Gosselin
Francis
F
O'Shea
Paul D
PD
Marcoux
Jean-François
JF
Angelaud
Rémy
R
Davies
Ian W
IW
D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis; D007659:Ketones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008670:Metals / Q000737:chemistry; D011407:Propane / Q000031:analogs & derivatives / Q000138:chemical synthesis; D012997:Solvents; D021241:Spectrometry, Mass, Electrospray Ionization; D028561:Transition Elements / Q000737:chemistry*
C518866:1-(3-bromo-4-methylphenyl)propan-2-one; D006842:Hydrocarbons, Brominated; D007659:Ketones; D008670:Metals; D012997:Solvents; D028561:Transition Elements; D011407:Propane