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2,6-Di(hetero)aryl and 2-(hetero)aryl substituted dithienothiazines are prepared from N-aryl dithienothiazines by a lithiation–lithium–zinc exchange–Negishi cross-coupling sequence with (hetero)aryl iodides in a one-pot fashion in good to excellent yields. These novel extended π-electron systems can be reversibly oxidized and fine-tuned in their electronic properties as supported by cyclo voltammetric, and absorption and emission spectroscopic studies.

organic chemistry frontiers

A one-pot dilithiation–lithium–zinc exchange–Negishi coupling approach to 2,6-di(hetero)aryl substituted dithienothiazines – a novel class of electronically fine-tunable redox systems