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- Title
Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On‐Water Conditions.
- Authors
La Manna, Pellegrino; Soriente, Annunziata; De Rosa, Margherita; Buonerba, Antonio; Talotta, Carmen; Gaeta, Carmine; Neri, Placido
- Abstract
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.
- Subjects
HETEROARENES; BENZYL chloride; AROMATIC compounds; SUPRAMOLECULAR chemistry; BENZENE
- Publication
ChemSusChem, 2019, Vol 12, Issue 8, p1673
- ISSN
1864-5631
- Publication type
Academic Journal
- DOI
10.1002/cssc.201900137