Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α‑Aminophosphonates

Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α‑Aminophosphonates

The widespread occurrence and synthetic accessibility of amides render them valuable precursors for the synthesis of diverse nitrogen-containing compounds. Herein, we present a metal-free and streamlined synthetic strategy for the synthesis of quaternary α-aminophosphonates. This approach involves s...

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Veröffentlicht in:Journal of the American Chemical Society 2024-02, Vol.146 (7), p.4357-4362
Hauptverfasser: Lu, Jiaxiang, Li, Zhenghua, Deng, Li
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creator Lu, Jiaxiang
Li, Zhenghua
Deng, Li
description The widespread occurrence and synthetic accessibility of amides render them valuable precursors for the synthesis of diverse nitrogen-containing compounds. Herein, we present a metal-free and streamlined synthetic strategy for the synthesis of quaternary α-aminophosphonates. This approach involves sequential deoxygenative nucleophilic phosphonation and versatile electrophilic alkylation of secondary amides in a one-pot fashion. Notably, this method enables the direct bis-functionalization of secondary amides with both nucleophiles and electrophiles for the first time, with simple derivatization leading to valuable free α-aminophosphonates by hydrolysis. The protocol has the advantages of operational simplicity, broad functional-group compatibility, environmental friendliness, and scalability to multigram quantities.
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title Deoxygenative Nucleophilic Phosphonation and Electrophilic Alkylation of Secondary Amides: A Facile Access to Quaternary α‑Aminophosphonates
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