17th Brazilian Meeting on Organic Synthesis

1,4-Naphthoquinones (1,4-NQs) are considered privileged structures implicated in several biological processes. Due of their biological importance, scientific endeavor has been devoted aiming at new synthetic methods for preparing 1,4-NQs with potential applicability against illness such as Chagas disease. Recently, our research group have demonstrated the effectiveness of [RhCp*Cl2]2 for the first catalytic directed ortho-functionalizations of simple (non-bias) 1,4-NQs by using different electrophilic iodine or bromine sources. This methodology opened way for new modification on the benzenoid ring of 1,4-NQs, as for example, by using copper catalyzed organoyl-thiolation reactions. Herein our strategy was based on the general and powerful method to install iodine at C-5 with high yield and regioselectivity and subsequently to combine an in situ generated ArSe- source (Santi reactant) with a copper catalyst, achieving the selenated adducts in only two steps via a direct sequential C-H iodination/organoyl-selenation protocol.