Please use this identifier to cite or link to this item: https://hdl.handle.net/2440/89301
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Type: Journal article
Title: Review on modern advances of chemical methods for the introduction of a phosphonic acid group
Author: Demmer, C.
Krogsgaard-Larsen, N.
Bunch, L.
Citation: Chemical Reviews, 2011; 111(12):7981-8006
Publisher: American Chemical Society
Issue Date: 2011
ISSN: 0009-2665
1520-6890
Statement of
Responsibility: 
Charles S. Demmer, Niels Krogsgaard-Larsen, and Lennart Bunch
Abstract: An overview of the physical-organic chemistry properties of the phosphonic acid group in connection to medicinal chemistry aspects is presented. A review on advances and modern synthetic methods for its introduction with respect to substrate-carbon hybridization is also presented. An alternative approach for the introduction of a dialkyl phosphonate group on to a benzyl halide is by a palladium(0)-catalyzed crosscoupling reaction, originally developed by Laven et al. In the presence of the Pd(O) catalyst [Pd 2(dba) 3(CHCl 3)] and Xantphos, a reactive Pd(O) Xantphos complex is formed, which undergoes oxidative addition to the benzyl halide substrate. Gelman et al. reported a method for the synthesis of aryl- and vinyl-phosphonic acids using copper(I) iodide and Cs 2CO 3 as base in toluene. Ishii et al. have developed a method for the addition H-phosphonate to nucleophilic alkenes, which relies on the use of MnOAc) 2 as catalyst.
Keywords: Phosphorous Acids
Carbon
Copper
Manganese
Molybdenum
Nickel
Palladium
Zinc Oxide
Catalysis
Chemistry, Organic
Chemical Phenomena
Organophosphonates
Rights: Copyright © 2011 American Chemical Society
DOI: 10.1021/cr2002646
Appears in Collections:Aurora harvest 7
Physics publications

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