Construction of Cyclopenta[ b ]pyridine Frameworks via Pd(0) π-Lewis Base-Initiated Cascade Reaction of Enyne-Tethered Malononitriles

Organic Letters 2026

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Authors: Shuo Li, Shu-Qian Wang, Ming-Si Feng, Ao Li, Zhi‐Chao Chen, Wei Du, Ying‐Chun Chen
DOI: 10.1021/acs.orglett.6c00158
Cited by: 0
References: 29

Abstract

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.

Fields of Study & Subjects

Catalytic Alkyne Reactions Catalytic Cross-Coupling Reactions Asymmetric Synthesis and Catalysis

Publication details

Journal / source
Organic Letters
Volume
28
Issue
8
Pages
2683–2687
Publication date
16 February 2026
Language
EN