22807-99-4Relevant articles and documents
Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions
La Manna, Pellegrino,Soriente, Annunziata,De Rosa, Margherita,Buonerba, Antonio,Talotta, Carmen,Gaeta, Carmine,Neri, Placido
, p. 1673 - 1683 (2019/03/26)
Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.
INTRODUCTION OF ALKYL SUBSTITUENTS TO AROMATIC COMPOUNDS
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Page/Page column 63, (2016/09/15)
Novel selective synthesis route to introduce primary alkyl groups on aromatic compounds is disclosed. The synthesis route is based on electrophilic aromatic substitutions of thionium ion species that are generated in-situ from aldehydes and thiols, affording benzyl sulfide that can be reduced with triethylsilane.
Hydrosilanes are not always a reducing reagent: A ruthenium-catalyzed introduction of primary alkyl groups to electron-rich aromatic rings using esters as a source of the alkyl groups
Nagashima, Hideo,Kubo, Yuichi,Kawamura, Mitsunobu,Nishikata, Takashi,Motoyama, Yukihiro
supporting information; experimental part, p. 7667 - 7672 (2011/10/19)
A triruthenium cluster, (μ3, η2, η3, η5-acenaphthylene)Ru3(CO) 7 effectively catalyzes primary-alkylation reaction of electron-rich aromatic rings using a combination of hydrosilane and est
