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The first metal-free alkynylation/ring expansion cascade process of alkenyl cyclobutanols with ethynylbenziodoxolones has been developed. A variety of synthetically valuable β-alkynylated cyclopentanones were prepared in moderate to good yields. Alkynyl cyclobutanols could also undergo this transformation, providing a new approach to substituted ene-yne-carbonyl compounds.

A copper-catalyzed reaction providing direct access to 2-arylpyridines from acetophenones and 1,3-diaminopropane is described. A range of electronically diverse acetophenones undergo this transformation, affording 2-arylpyridines in good yields.

An efficient, concise, and transition metal-free synthesis of functionalized sulfonylated five-membered heterocyclic compounds via an S(N)Ar reaction has been developed. Using commercially available sodium sulfinates as sulfonylation reagents, various five-membered heterocyclic sulfones were obtained in good yields.