Tropylium cation now serves as an organocatalyst

Abstract

The tropylium ion is a curious seven-membered aromatic ring (C7H7+) used in organic synthesis and as a ligand for metal complexes. Chemists led by T. Vinh Nguyen of the University of New South Wales Sydney have shown for the first time that tropylium salts can act as organic Lewis acid catalysts (Green Chem. 2017, DOI: 10.1039/c7gc01519d). Carbonyl compounds used in multistep reactions are often temporarily functionalized via acetalization reactions to mask their reactivity. This protection step typically relies on a metal salt Lewis acid catalyst. But residual metal can pose problems in purifying pharmaceutical products, leading to excessive use of solvents and generating waste. Organocatalysts that avoid metals are often a greener option. Building on their prior research on tropylium chemistry, Nguyen and coworkers reasoned that the carbocation with one positive charge delocalized over the conjugated seven-membered ring could serve as a “soft Lewis catalyst” for protective acetalizations of aldehydes