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Laboratory study demonstrates divergent electrochemical cyclization of isothiocyanates and allylamines into diverse sulfur heterocycles, highlighting substrate-controlled reaction pathways.
A KI-mediated electrochemical tandem addition/cyclization of isothiocyanates with allylamines affords thiazolidin-2-imines and benzothiazole-type products in an undivided cell. The protocol provides 53 products, including drug-derived substrates. Product-distribution studies and DFT calculations reveal substrate-controlled competition between 5-exo-trig alkene cyclization and arene C–S annulation: phenyl systems favor alkene cyclization, whereas strongly activated or π-extended arenes favor arene annulation. Mechanistic experiments support an iodide-enabled radical pathway.
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Li et al. (2026) studied this question.
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