77561-95-6

Upstream product

• 593-56-6 N-methoxylamine hydrochloride 
• 532-27-4 1-chloroacetophenone 

Downstream Products

• 163586-90-1 (E)-1,2-diphenylethanone O-methyl oxime 
• 15754-20-8 (E)-acetophenone O-methyloxime 
• 146364-41-2 (E)-2-(4-methoxyphenyl)-1-phenylethanone O-methyloxime 
• 113694-72-7 (E)-1-phenyl-2-p-tolylethanone O-methyloxime 
• 1361387-66-7 (E)-1-(furan-2-yl)-3-(methoxyimino)-3-phenylpropan-1-one 
• 1361387-64-5 (E)-3-(methoxyimino)-1,3-diphenylpropan-1-one 

Relevant academic research and scientific papers

Palladium-catalyzed suzuki carbonylative reaction of a-halomethyl oxime ethers: A regioselective route to unsymmetrical 1,3-oxyiminoketones

The three-component reaction of a-halomethyl oxime ethers, boronic acids and carbon monoxide at atmospheric pressure catalyzed by tetrakis- (triphenylphosphine)palladium(0) gives efficiently unsymmetrical b-alkoxyimino carbonyl compounds with total control of the regioselectivity, in high yield and atomic economy. Simple commercially available starting materials are used in this synthetic procedure. The three components assembly takes place preferentially versus the competing direct coupling or other possible side reactions. The mechanism of the transformation was investigated by NMR and intermediate palladium(II) complexes were detected.

Palladium-catalyzed suzuki-miyaura cross-coupling of a-halomethyl oxime ethers and site-selective cross-coupling of dihalo derivatives

The cross-coupling reaction of chloro- and bromomethyl oxime ethers with a wide range of aryl-, heteroaryl- and vinylboronic acids in the presence of catalytic palladium complexes with different phosphines has been carried out with good yields (60-98%, 40 examples). Regioselective cross-coupling reactions differentiating between an alkyl or aryl position are achieved from dihalo oxime ethers containing Csp2- and Csp3-halogen bonds using mono- or dicoordinated palladium catalysts such as Pd (dba)2/P (o-tolyl)3 or Pd (PPh3)4. The selective orthogonal functionalization of dihalo oxime ethers is also described. Site-selective transformations allow the introduction of the biaryl motif into dihalo oxime ethers preserving the highly activated alkyl halide moiety vicinal to the oxime group for further transformations. In this context, Z- and E-oxime ethers could be considered as synthetic equivalents of ketones in palladium-catalyzed Suzuki reactions.