Metal-Free Oxidative Radical Alkynylation/Ring Expansion Rearrangement of Alkenyl Cyclobutanols with Ethynylbenziodoxolones.

The first metal-free alkynylation/ring expansion cascade process of alkenyl cyclobutanols with ethynylbenziodoxolones has been developed. A variety of synthetically valuable ß-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.

Iodine-mediated synthesis of 3-acylbenzothiadiazine 1,1-dioxides.

An iodine-mediated synthesis of 3-acylbenzothiadizine 1,1-dioxides is described. A range of electronically diverse acetophenones reacted well with several 2-aminobenzenesulfonamides, affording 3-acylbenzothiadiazine 1,1-dioxides in good yields.

An efficient synthesis of quinolines via copper-catalyzed C-N cleavage.

An efficient method to synthesize substituted quinolines from ketones and 2-amino benzylamines is described. Copper-catalyzed C-N cleavage of amines followed by condensation with ketones deliver quinolines in moderate to high yields. The broad scope of substrates and the use of air as the sole oxidant make this transformation very attractive.

Copper-catalyzed aerobic synthesis of 2-arylpyridines from acetophenones and 1,3-diaminopropane.

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.

Sulfonylation of five-membered heterocycles via an S(N)Ar reaction.

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.