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We report on the implementation of the concept of a photochemically elicited two‐carbon homologation of a π‐donor–π‐acceptor substituted chromophore by triple‐bond insertion. Implementing a phenyl connector between the slide‐in module and the chromophore enabled the synthesis of cylohepta[b]indole‐type building blocks by a metal‐free annulative one‐pot two‐carbon ring expansion of the five‐membered...
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