Solid supported synthesis of phosphinates via palladium (0) catalysed coupling reactions.
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 alpha-hydroxy, alpha-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).
Haaf
Klaus
K
Bayer CropScience GmbH, Chemistry Frankfurt (G836), Industriepark Höchst, 65926 Frankfurt am Main, Germany. Klaus.Haaf@bayercropscience.com
D016573:Agrochemicals / Q000138:chemical synthesis*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006540:Herbicides / Q000138:chemical synthesis; D010165:Palladium; D010757:Phosphorous Acids / Q000138:chemical synthesis*
D016573:Agrochemicals; D006540:Herbicides; D010757:Phosphorous Acids; D010165:Palladium; C043639:metaphosphoric acid