Three different modes of aldehyde/alkyne assembly through a controlled radical reaction are devised. While a double C−H activation/annulation leads to indenones, a concurrent oxidation of both aldehydes and alkynes in the course of their connection offers aroyloxy ketones. Besides two types of cascade reactions starting from identical materials, through a phenylpropiolic acid substrate, a cascade three C−C bond formation via an uninterrupted C−H functionalization/annulation/decarboxylative aroylation as a formidable challenge in radical reactions occurs to deliver 2-aroyl-3-aryl indenones.
A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C–S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.
A novel regioselective annulation of propargylic alcohols
with
simple carbazoles for the construction of [3,2,1-jk]carbazole scaffolds is described to be the first example of intermolecular
synthesis of [3,2,1-jk]carbazoles from simple carbazoles. In situ synthesis of propargyl alcohols from simple, cheap,
and easily accessible ketones has also been developed during the one-pot
synthesis of [3,2,1-jk]carbazoles.
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