AI Article Synopsis
- Amides are important as starting materials for creating various nitrogen-containing compounds due to their availability and easy synthesis.
- The study introduces a new method to produce quaternary α-aminophosphonates using a simple, one-pot reaction that employs secondary amides and involves both phosphonation and alkylation.
- This innovative process is eco-friendly, easy to execute, works with a wide range of chemical groups, and can be scaled up for larger quantities, making it efficient for practical use.
Article Abstract
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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| http://dx.doi.org/10.1021/jacs.3c14517 | DOI Listing |
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