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Synthesis of P-Containing Polycyclic Aromatic Hydrocarbons from Alkynyl-phosphonium Salts.

Yijie WangGuangchen SuMingsheng LiLi YaoWesley A ChalifouxWenlong Yang
Published in: Organic letters (2024)
This work presents a straightforward method for synthesizing a series of phosphorus-containing polycyclic aromatic hydrocarbons (P-PAHs) featuring an internal ylidic bond. The method involves anion exchange, alkyne annulation, and deprotonation reactions, enabling the efficient production of cyclic phosphonium salts, which serve as pivotal intermediates in the synthesis of P-PAHs. The alkyne annulation reaction exhibits high regioselectivity, ensuring the successful synthesis of λ 5 -phosphaphenanthrene isomers. Additionally, the incorporation of electron-withdrawing groups effectively stabilizes the internal ylidic bond of P-PAHs.
Keyphrases
  • polycyclic aromatic hydrocarbons
  • ionic liquid
  • electron transfer
  • climate change
  • heavy metals
  • solar cells