Solid Supported Synthesis of Phosphinates Via Palladium (0) Catalysed Coupling Reactions

Title: Solid Supported Synthesis of Phosphinates Via Palladium (0) Catalysed Coupling Reactions

Volume: 8 Issue: 7

Author(s): Klaus Haaf

Affiliation:

Keywords: aryl phosphinates, palladium coupling, solid phase synthesis

Abstract: In order to gain a broad access to phosphinic acid derivatives, a palladium catalysed coupling reaction of aryl iodides with hypophosphorous acid derivatives has been developed on the solid phase. The resulting arylphosphorous acids (or esters) were derivatised using addition reactions with aldehydes, imines and isocyanates, to give phosphinic acids (or esters) with α-hydroxy , α-amino or aminoacyl groups attached to the aryl phosphorus moiety. This approach provided a broad chemical entry into a class of polar phosphinates compounds which were rather difficult to handle using normal solution phase synthesis. The synthetic potential of this solid phase based methodology was demonstrated by the synthesis of targeted libraries against the enzyme dihydrodipicolinate synthase (DHDPS).

Cite this article as:

Haaf Klaus, Solid Supported Synthesis of Phosphinates Via Palladium (0) Catalysed Coupling Reactions, Combinatorial Chemistry & High Throughput Screening 2005; 8 (7) . https://dx.doi.org/10.2174/138620705774575382