223396-66-5Relevant academic research and scientific papers
Palladium-catalyzed intramolecular α-arylation of aliphatic ketone, formyl, and nitro groups
Muratake, Hideaki,Natsume, Mitsutaka,Nakai, Hiroshi
, p. 11783 - 11803 (2007/10/03)
Intramolecular arylation of properly designed substrates bearing a ketone, formyl, or nitro terminating group was achieved by use of a PdCl 2(Ph3P)2-Cs2CO3 reaction system to form a variety of carbocyclic compounds. Arylation in ketone compounds afforded benzene-annulated bridged or spirocycloalkanone derivatives, depending on the structure of the cyclization precursors. Arylation in formyl compounds occurred at the α-position (α-arylation) or at the carbonyl carbon (carbonyl-arylation) depending on the structure of the cyclization precursors and on the reaction solvent. An α-arylated secondary nitro group was partially transformed to ketone in the manner of the Nef reaction, whereas a tertiary nitro group was partially eliminated to afford a styrene-type olefin. Graphical Abstract
