Trichloroisocyanuric Acid-Promoted Synthesis of Arylselenides and Aryltellurides from Diorganyl Dichalcogenides and Arylboronic Acids at Ambient Temperature

A transition-metal-free method for the synthesis of arylselenides and aryltellurides has been established based on the oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids. With trichloroisocyanuric acid as an oxidant, the reaction proceeded smoothly to afford the desired products in 45-97% yields at ambient temperature. Three reaction reagents used in this method are stoichiometric and the oxidation by-product isocyanuric acid can be easily isolated and recovered. Besides of arylboronic acids, aryl trifluoroborates and aryl trihydroxyborates salts are also able to perform this transformation.

Automated summary

A transition-metal-free method for synthesizing arylselenides and aryltellurides has been established through oxidative cross-coupling between diorganyl dichalcogenides and aryl boronic acids using trichloroisocyanuric acid as an oxidant. The reaction proceeds smoothly at ambient temperature with high yields. In addition to aryl boronic acids, other compounds such as aryl trifluoroborates and aryl trihydroxyborates salts can also undergo this transformation.