Abstract
In organic chemistry, dimerization reactions represent a synthetically powerful strategy for the rapid construction of molecular complexity. This study introduces a copper-catalyzed radical dimerization of 1-alkynylnaphthols, enabling chemo- and diastereoselective synthesis of bridged tetrahydro-benzo[no]tetraphenone products. The approach boasts the use of an economical catalyst and a green oxidant under mild conditions. Different heteroaryls, such as indole and thiophene, are well-tolerated in the reaction. Control experiments provided valuable insights, revealing a sequence involving the formation of a C1–radical intermediate, intermolecular (3+2) cyclization, and an unusual intramolecular C4–C8′ coupling.
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