Chemical synthesis study demonstrates transition-metal-free intramolecular Csp2–Csp3 coupling of aromatic amides via photoinduced azaxylylene cascades, enabling efficient access to polyheterocycles.
A new mode for complexity-building photochemical cascades which offers experimentally simple transition metal-free intramolecular C sp 2 –C sp 3 cross coupling of aromatic amides is attained via an unprecedented [2 + 2] reactivity of ESIPT-generated azaxylylenes. Coupled with short and straightforward postphotochemical modifications of the primary photoproducts, these cascades allow for a significant step-normalized growth of molecular complexity while accessing diverse and complex polyheterocyclic molecular architectures.
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Reddy et al. (2023) studied this question.
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