Demonstrates the synthesis of cyclopenta[b]pyridines in malononitrile derivatives, suggesting a new method for complex organic molecules.
A Pd(0) π-Lewis base-initiated cascade transformation of 1,3-enyne-tethered malononitriles is disclosed, proceeding through intramolecular vinylogous addition of the nucleophilicity-enhanced alkyne moiety to a pendent cyano group, cis/trans isomerization, and Suzuki coupling, followed by 6π-aza-electrocyclization and oxidative aromatization. A range of cyclopenta[b]pyridines are constructed straightforwardly, while azafluorenes are obtained instead in the presence of formic acid. Moderate enantioselectivity is also achieved using a chiral sulfinamide-phosphine ligand.
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Li et al. (2026) studied this question.
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