Abstract Alkyne-based regioselective functionalization is an important transformation method for the synthesis of a wide variety of organic products. In this work, a regioselective TBAI-mediated oxidative 5-exo-dig iodo-oxycyclization of 2-alkynylbenzamide… Click to show full abstract
Abstract Alkyne-based regioselective functionalization is an important transformation method for the synthesis of a wide variety of organic products. In this work, a regioselective TBAI-mediated oxidative 5-exo-dig iodo-oxycyclization of 2-alkynylbenzamide is used for the synthesis of various isobenzofuran derivatives with excellent functional group tolerance and high reaction efficiency. We hypothesized that using water in a mixed solvent could change the reaction pathway and realize a high reaction regioselectivity. Furthermore, the application of the developed procedure was demonstrated by the synthesis of phthalazin-1(2H)-one and aryl-substituted isobenzofurans.
Journal Title: Tetrahedron
Year Published: 2018
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