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Published on: April 22, 2016
Synthesis of γ-Aminophosphonates via Photocatalytic Radical Relay Process
Kui Zhang1, Yang Chen1, Xueping Zhang1
1State Key Laboratory for Development and Utilization of Forest Food Resources, Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, International Innovation Center for Forest Chemicals and Materials, Jiangsu Province Key Laboratory of Green Biomass-Based Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China.
This study introduces a new photocatalytic method for synthesizing gamma-aminophosphonates using readily available oxime esters. This efficient approach offers broad applicability and enables further conversion into valuable azaphosphorus heterocycles.
Area of Science:
- Organic Chemistry
- Medicinal Chemistry
- Photocatalysis
Background:
- Gamma-aminophosphonates possess significant biological activities and therapeutic potential.
- Existing synthetic routes for gamma-aminophosphonates are often inefficient or limited in scope.
Purpose of the Study:
- To develop a novel, mild, and efficient photocatalytic method for synthesizing gamma-aminophosphonates.
- To utilize easily accessible oxime esters as precursors in a radical relay process.
Main Methods:
- A photocatalytic strategy employing aryl radical-initiated radical relay.
- Use of oxime esters as dual precursors for phenyl and iminyl radicals.
- Exploration of substrate scope and functional group tolerance.
Main Results:
- Successful construction of diverse gamma-aminophosphonates under mild conditions.
- Demonstrated broad substrate scope and excellent functional group tolerance.
- Products were successfully transformed into complex azaphosphorus heterocycles.
Conclusions:
- The developed photocatalytic method provides an efficient and versatile route to gamma-aminophosphonates.
- This strategy expands the synthetic toolkit for accessing important organophosphorus compounds.
- The methodology facilitates the synthesis of novel azaphosphorus heterocycles for potential medicinal applications.
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