Electrochemical synthesis of heterodehydro[7]helicenes.

ABSTRACT: Dehydrohelicenes are some of the most attractive chiroptical materials with unique helical chirality. However, to our knowledge, there are no prior reports on their direct construction by asymmetric methods. In this work, sequential synthesis of aza-oxa-dehydro[7]helicenes via the electrochemical oxidative hetero-coupling of 3-hydoxycarbazoles and 2-naphthols followed by dehydrative cyclization and intramolecular C-C bond formation has been realized. In addition, an efficient enantioselective synthesis through chiral vanadium-catalyzed hetero-coupling and electrochemical oxidative transformations afforded heterodehydro[7]helicene without any racemization. The obtained dehydro[7]helicenes showed intense blue-colored circularly polarized luminescence (|g_lum| ≈ 2.5 × 10^-3

SUBMITTER: Khalid MI 

PROVIDER: S-EPMC9814689 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature