Facile Synthesis of π-Conjugated Heteroaromatic Compounds via Weak-Base-Promoted Transition-Metal-Free C–N Coupling

Abstract

A K₂CO₃-promoted transition-metal-free C–N coupling reaction was developed. When a solution of 1-(2-aminophenyl)-8-iodo­naphthalenes in DMSO was treated with 2.5 equivalents of K₂CO₃ and 5.0 equivalents of MeI, intramolecular C–N coupling reaction proceeded smoothly even at low temperature (room temperature) to afford various heteroaromatic compounds in good chemical yields. Additional experiments suggested that this reaction might have proceeded through an unusual S_NAr reaction between haloarenes and a bulky tertiary amine moiety.

Key words

heterocycles - coupling - metal-free - π-conjugated molecule - base-promoted reaction

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