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An exclusive thiophene-fused polycyclic π-conjugated 2-arylbenzo­[4,5]­thieno­[2,3-d]­thiazole skeleton was constructed via a one-pot CuCl-mediated three-component reaction, using 2-(2-bromophenyl)­acetonitrile and aromatic aldehydes as substrates and elemental sulfur as sulfur source in the presence of K2CO3 and 1,10-phen in DMSO. A plausible reaction mechanism was proposed, which involved formation of benzo­[b]­thiophen-2-amines through cyclization of 2-bromophenyl acetonitrile and sulfur, and subsequent intramolecular condensation/dehydrogenation with aromatic aldehydes.

The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.

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