Abstract

Heteroaromatic compounds have been shown to play a crucial role in several disciplines such as materials chemistry, agrochemical and pharmaceutical industry. Hence, there has been a great emphasis on the development of methodologies for the synthesis of such motifs. Generally, the formation of the new carbon-carbon bond in connecting two aromatic systems can be achieved by the palladium-catalyzed cross-coupling reactions. Although, classic synthetic routes are effective, they may involve the use of harsh reaction conditions and potentially dangerous pre-functionalization of organometallic reagents. More recently, attention has been turned towards the development of more efficient novel methodologies employing more environmental benign and alternative reaction conditions, such as C-H activation, decarboxylative and desulfinative cross-coupling reactions. The advantage of the decarboxylative and desulfinative cross-coupling lies in their ability to be chemo-selective while producing minor amounts of gas as byproduct. Most of the synthetic routes use aryl halides as a coupling partner for the formation of these motifs. Herein, to expand the tool kit, we developed new synthetic routes through the use of diaryliodonium salts to replace aryl halides in accessing heteroaromatics through decarboxylative and desulfinative palladium-catalyzed cross-coupling reactions. Diaryliodonium salts have emerged as a highly versatile reactant applicable in numerous organic reactions. Their structure provides them with the potential to be a more reactive coupling partner in comparison to aryl-halides. In an effort to further improve the decarboxylative cross-coupling reactions, their applicability in the methodology. Furthermore, the reactions of diaryliodonium salts with sulfinate salts in cross-coupling reactions has not been examined to date, creation of a methodology utilizing these compounds could potentially be a big step in these classes of reactions.