Visible-Light-Induced 1,6-Enynes Triggered C–Br Bond Homolysis of Bromomalonates: Solvent-Controlled Divergent Synthesis of Carbonylated and Hydroxylated Benzofurans
Jiupeng Liu, Shuo Tang, Shichong Wang, Mengting Cao, Jingjing Zhao, Puyu Zhang, Pan Li
Abstract
Visible-light-induced 1,6-enyne-triggered C-Br bond homolysis of bromomalonates has been developed. This transition-metal-free, photocatalyst-free, and oxidant- and additive-free protocol affords an efficient approach for divergent synthesis of carbonylated and hydroxylated benzofurans from 1,6-enynes and bromomalonates under mild conditions. Significantly, mechanistic studies reveal that the homolysis of C-Br bonds appears to experience an energy-transfer pathway, and the atom-transfer radical addition products are the key intermediates to generate carbonylated and hydroxylated benzofurans.
Topics & Concepts
HomolysisChemistryPhotochemistryDeoxygenationEnyneOxidative phosphorylationStereochemistryRadicalOrganic chemistryCatalysisBiochemistryRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques