Metallic nickel-mediated synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides

Journal Article · Fri May 03 04:00:00 EDT 1985 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00209a006· OSTI ID:5227421

Inaba, S; Rieke, R D

Metallic nickel was investigated as a convenient coupling reagent for the synthesis of ketones by the reaction of benzylic, allylic, vinylic, and pentafluorophenyl halides with acid halides at 85/sup 0/C in glyme. A variety of benzylic ketones with functional groups including halogen, cyano, methoxycarbonyl, and hydroxycarbonyl groups were prepared in good yields by this method. The reaction was demonstrated to proceed via organonickel halide intermediates formed by the smooth oxidative addition of benzylic and acyl halides to metallic nickel, which were trapped with electron-deficient olefins. (..pi..-Allyl)nickel halides, prepared in situ at 85/sup 0/C from allylic halides and the nickel, also worked for the preparation of ketones. Vinylic and pentafluorophenyl halides but not alkyl halides reacted with acid halides to give the corresponding ketones in moderate yields. 95 references, 3 tables.

• Research Organization: Univ. of Nebraska, Lincoln
• DOE Contract Number: AC02-80ER10603
• OSTI ID: 5227421
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 50:9; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
CHEMICAL REACTIONS
COUPLING
DATA
EXPERIMENTAL DATA
HALIDES
HALOGEN COMPOUNDS
INFORMATION
KETONES
MEDIUM TEMPERATURE
NICKEL COMPOUNDS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
OXIDATION
SYNTHESIS
TRANSITION ELEMENT COMPOUNDS