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

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...

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Veröffentlicht in:	Organic letters 2024-06, Vol.26 (25), p.5280-5284
Hauptverfasser:	Wang, Yijie, Su, Guangchen, Li, Mingsheng, Yao, Li, Chalifoux, Wesley A., Yang, Wenlong
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Sprache:	eng
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creator	Wang, Yijie Su, Guangchen Li, Mingsheng Yao, Li Chalifoux, Wesley A. Yang, Wenlong
description	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 λ5-phosphaphenanthrene isomers. Additionally, the incorporation of electron-withdrawing groups effectively stabilizes the internal ylidic bond of P-PAHs.
doi_str_mv	10.1021/acs.orglett.4c01579
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title	Synthesis of P‑Containing Polycyclic Aromatic Hydrocarbons from Alkynyl-phosphonium Salts
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