Literature DB >> 16928101

Palladium-catalyzed dehydrative allylation of hypophosphorous acid with allylic alcohols.

Karla Bravo-Altamirano1, Jean-Luc Montchamp.   

Abstract

A novel palladium-catalyzed allylation of H3PO2 with allylic alcohols is described. The phosphorus-carbon bond-forming reaction produces allylic-H-phosphinic acids and water, in the absence of additives. Primary H-phosphinic acids are obtained in excellent yields, whereas secondary H-phosphinic acids react sluggishly. A reusable polymer-supported catalyst is also described. The reaction provides an environmentally sound approach to H-phosphinic acids.

Entities:  

Year:  2006        PMID: 16928101     DOI: 10.1021/ol061828e

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  8 in total

1.  Palladium-catalyzed allylic substitution with (η6-arene-CH2Z)Cr(CO)(3)-based nucleophiles.

Authors:  Jiadi Zhang; Corneliu Stanciu; Beibei Wang; Mahmud M Hussain; Chao-Shan Da; Patrick J Carroll; Spencer D Dreher; Patrick J Walsh
Journal:  J Am Chem Soc       Date:  2011-11-29       Impact factor: 15.419

2.  Submicromolar phosphinic inhibitors of Escherichia coli aspartate transcarbamoylase.

Authors:  Laëtitia Coudray; Evan R Kantrowitz; Jean-Luc Montchamp
Journal:  Bioorg Med Chem Lett       Date:  2008-12-06       Impact factor: 2.823

3.  Green, Palladium-Catalyzed Synthesis of Benzylic H-phosphinates from Hypophosphorous Acid and Benzylic Alcohols.

Authors:  Laëtitia Coudray; Jean-Luc Montchamp
Journal:  European J Org Chem       Date:  2008-08-01

4.  A novel approach to phosphonic acids from hypophosphorous acid.

Authors:  Karla Bravo-Altamirano; Jean-Luc Montchamp
Journal:  Tetrahedron Lett       Date:  2007-08-13       Impact factor: 2.415

5.  Recent Developments in the Addition of Phosphinylidene-Containing Compounds to Unactivated Unsaturated Hydrocarbons: Phosphorus-Carbon Bond-Formation via Hydrophosphinylation and Related Processes.

Authors:  Laëtitia Coudray; Jean-Luc Montchamp
Journal:  European J Org Chem       Date:  2008-07-01

6.  Revisiting the Hirao Cross-coupling: Improved Synthesis of Aryl and Heteroaryl Phosphonates.

Authors:  Yamina Belabassi; Saeed Alzghari; Jean-Luc Montchamp
Journal:  J Organomet Chem       Date:  2008-01-15       Impact factor: 2.369

7.  Temporary Protection of H-Phosphinic Acids as a Synthetic Strategy.

Authors:  Laëtitia Coudray; Jean-Luc Montchamp
Journal:  European J Org Chem       Date:  2009-09

Review 8.  Let's Make White Phosphorus Obsolete.

Authors:  Michael B Geeson; Christopher C Cummins
Journal:  ACS Cent Sci       Date:  2020-05-18       Impact factor: 14.553

  8 in total

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