Synthesis of Saccharinyl Substituted Aromatic Compounds Using Stoichiometric Amounts of Copper(I)
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Addition of [bis(saccharinyl)iodo]benzene to a methylene chloride solution of Phen-Cu-Sac resulted in electrophilic aromatic substitution of saccharine onto toluene. Similar reactions occurred with benzene and anisole. Umpolung reactivity allowed for the formation of electrophilic saccharine cations. Sodium saccharine contaminated [bis(saccharinyl)iodo]benzene afforded higher yields of the saccharinyl substituted aromatic by allowing the saccharine cation to form from the copper (I) complex before oxidizing to copper (II). A mechanism for the optimized reaction is presented.