Iodine(iii) reagents have attracted chemical importance in organic synthesis by their use as safe, non-toxic, green and easy to handle reagents in different transformations.

A catalytic, practical and high-yielding procedure for the synthesis of indenes by direct C_sp3–H activation under gold(i) catalysis was developed.

The chemoselective reaction of the C- followed by the O-centered naphthyl radicals with the more electron-deficient hypervalent bond of the diaryliodonium(III) salts is described. This discovered reactivity constitutes a new activation mode of the diaryliodonium(III) salts which enabled a one-pot doubly arylation of naphthols through the sequential ${\text{C}}_{sp}^2$-${\text{C}}_{sp}^2$/O-${\text{C}}_{sp}^2$ bond formation. The naphthyl radicals were generated in the reaction by the tetramethylpiperidinyl radical (TMP·) which resulted from the homolytic fragmentation of the precursor TMP₂O. Experimental and DFT calculations provided a complete panorama of the reaction mechanism.

A practical, concise and straightforward total synthesis of kealiiquinone 1, a naphtho[2,3-d]imidazole alkaloid obtained from the Micronesian marine sponge Leucetta sp. was accomplished. The squaric acid chemistry to construct the 1,4-quinoid ring and the regioselective N-methylation through a benzo[c][1,2,5]selenadiazolium heterocycle are the key features in this report. The full details of the representative approaches involving the different attempted synthetic strategies are also presented. Finally a successful total synthesis of this complex secondary metabolite is described.