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Literature DB >> 22505878

Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

Laxmidhar Rout¹, Sridhar Regati, Cong-Gui Zhao.

Abstract

Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts were developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data.

Entities: CellLine Chemical Disease Gene

Year: 2011 PMID： 22505878 PMCID： PMC3324819 DOI： 10.1002/adsc.201100605

Source DB: PubMed Journal: Adv Synth Catal ISSN： 1615-4150 Impact factor: 5.837

30 in total

1. Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement.

Authors: Pierre-Yves Renard; Philippe Vayron; Eric Leclerc; Alain Valleix; Charles Mioskowski
Journal: Angew Chem Int Ed Engl Date: 2003-05-30 Impact factor: 15.336

2. Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

Authors: Sandun Perera; Vijaya Kumar Naganaboina; Long Wang; Bin Zhang; Qunsheng Guo; Laxmidhar Rout; Cong-Gui Zhao
Journal: Adv Synth Catal Date: 2011-06-30 Impact factor: 5.837

3. Nonpeptide inhibitors of cathepsin G: optimization of a novel beta-ketophosphonic acid lead by structure-based drug design.

Authors: Michael N Greco; Michael J Hawkins; Eugene T Powell; Harold R Almond; Thomas W Corcoran; Lawrence de Garavilla; Jack A Kauffman; Rosario Recacha; Debashish Chattopadhyay; Patricia Andrade-Gordon; Bruce E Maryanoff
Journal: J Am Chem Soc Date: 2002-04-17 Impact factor: 15.419

4. Copper catalyzed arylation/C-C bond activation: an approach toward alpha-aryl ketones.

Authors: Chuan He; Sheng Guo; Li Huang; Aiwen Lei
Journal: J Am Chem Soc Date: 2010-06-23 Impact factor: 15.419

5. Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures.

Authors: Xiaoan Xie; Yu Chen; Dawei Ma
Journal: J Am Chem Soc Date: 2006-12-20 Impact factor: 15.419

6. A novel, potent dual inhibitor of the leukocyte proteases cathepsin G and chymase: molecular mechanisms and anti-inflammatory activity in vivo.

Authors: Lawrence de Garavilla; Michael N Greco; Narayanasami Sukumar; Zhi-Wei Chen; Agustin O Pineda; F Scott Mathews; Enrico Di Cera; Edward C Giardino; Grace I Wells; Barbara J Haertlein; Jack A Kauffman; Thomas W Corcoran; Claudia K Derian; Annette J Eckardt; Bruce P Damiano; Patricia Andrade-Gordon; Bruce E Maryanoff
Journal: J Biol Chem Date: 2005-02-28 Impact factor: 5.157

Synthesis of α-Arylphosphonates Using Copper-Catalyzed α-Arylation and Deacylative α-Arylation of β-Ketophosphonates.

1. Lewis acid catalyzed room-temperature Michaelis-Arbuzov rearrangement.

2. Organocatalytic High Enantioselective Synthesis of β-Formyl-α-hydroxyphosphonates.

3. Nonpeptide inhibitors of cathepsin G: optimization of a novel beta-ketophosphonic acid lead by structure-based drug design.

4. Copper catalyzed arylation/C-C bond activation: an approach toward alpha-aryl ketones.

5. Enantioselective arylation of 2-methylacetoacetates catalyzed by CuI/trans-4-hydroxy-L-proline at low reaction temperatures.

6. A novel, potent dual inhibitor of the leukocyte proteases cathepsin G and chymase: molecular mechanisms and anti-inflammatory activity in vivo.

7. Enantioselective synthesis of alpha-aminopropargylphosphonates.

8. Copper/amino acid catalyzed cross-couplings of aryl and vinyl halides with nucleophiles.

9. Inhibition of purple acid phosphatase with alpha-alkoxynaphthylmethylphosphonic acids.

10. Room-temperature copper-catalyzed alpha-arylation of malonates.

1. Palladium-catalyzed α-arylation of benzylic phosphine oxides.

2. Route to α-Aryl Phosphonoacetates: Useful Synthetic Precursors in the Horner-Wadsworth-Emmons Olefination.

3. Palladium-catalyzed α-arylation of benzylic phosphonates.