4.8 Article

Palladium-Catalyzed Modular Synthesis of Enantioenriched Pyridohelicenes through Double Imidoylative Cyclization

Journal

ACS CATALYSIS
Volume 12, Issue 20, Pages 13034-13041

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c04461

Keywords

asymmetric synthesis; pyridohelicenes; palladium catalysis; functionalized isocyanide; helical chirality

Funding

  1. National Natural Science Foundation of China [21871268, 22071250, 21925112, 22271288, 22271287]
  2. Natural Science Foundation of Guangdong Province of China [2020A1515011428]
  3. BAGUI Scholar Program of Guangxi Province of China
  4. Guangzhou Branch of the Supercomputing Center of CAS
  5. SKLRD Project [SKLRD-Z-202014]

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Enantioenriched pyrido[6]helicenes and furan-containing pyrido[7]helicenes have been synthesized through a palladium-catalyzed double imidoylative cyclization. This method allows for the construction of two pyridyl rings in one pot, leading to structurally diverse optically pure pyridohelicenes. This research provides potential for optical studies and applications of this important class of azahelicenes.
Enantioenriched pyrido[6]helicenes and furan-containing pyrido[7]helicenes have been synthesized through palladium-catalyzed double imidoylative cyclization by applying axially achiral multiaryl bisisocyanides and aryl iodides as coupling components. Two pyridyl rings were constructed sequentially by forming four C-C bonds in one pot with low catalyst loading. A control study using precyclized biaryl monoisocyanides revealed the second pyridine-forming enantiomer-generating step, which also enabled the introduction of different substituents, including trifluoromethyl, on the helical skeleton. This general and convergent approach to structurally diversified optically pure pyridohelicenes paves the way for optical studies and potential applications of this important class of azahelicenes.

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