Photocatalytic Biheterocyclization of 1,7-Diynes for Accessing Skeletally Diverse Tricyclic 2-Pyranones
Lu Wang, Ting Xu, Qian Rao, Tian-Shu Zhang, Wen‐Juan Hao, Shu‐Jiang Tu, Bo Jiang
Abstract
A new and green route to skeletally diverse oxo-heterocyclic architectures such as pyrano[3,4-c]chromen-2-ones and pyrano[3,4-c]quinolin-2-ones is reported via an unprecedented photocatalytic Kharasch-type cyclization/1,5-(SN″)-substitution/elimination/6π-electrocyclization/double nucleophilic substitution cascade starting from easily available heteroatom-linked 1,7-diynes and low-cost CBrCl3. During this reaction process, the full scission of carbon–halogen bonds of BrCCl3 was realized to directly build two new rings, including a lactone scaffold, using H2O as the oxygen source of the ester group.
Topics & Concepts
ChemistryPhotocatalysisHeteroatomNucleophilic substitutionCombinatorial chemistryDouble bondHalogenNucleophileTricyclicRing (chemistry)Organic chemistryMedicinal chemistryCatalysisAlkylCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions