NiCl2-Catalyzed Hydrophosphinylation

A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor subst...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-05, Vol.70 (10), p.4064-4072
Main Authors: Ribière, Patrice, Bravo-Altamirano, Karla, Antczak, Monika I, Hawkins, Jennifer D, Montchamp, Jean-Luc
Format: Article
Language:English
Subjects:
Aliphatic compounds
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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Summary:A new nickel-based catalytic system has been developed for phosphorus−carbon bond formation. The addition of alkyl phosphinates to alkynes is catalyzed by nickel chloride in the absence of added ligand. The reaction generally proceeds in high yields, even with internal alkynes, which were poor substrates in our previously reported palladium-catalyzed hydrophosphinylation of alkyl phosphinates. The method is useful for the preparation of H-phosphinate esters and their derivatives. The one-pot synthesis of various important organophosphorus compounds is also demonstrated. The reaction can be conducted with microwave heating.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050096l