Direct conversion of secondary phosphine oxides and H-phosphinates with [Di(acyloxy)iodo]benzenes to phosphinic and phosphonic amides

✍ Scribed by Anna Hubacz; Slawomir Makowiec

• Publisher: John Wiley and Sons
• Year: 2009
• Tongue: English
• Weight: 142 KB
• Volume: 20
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.20514

✦ Synopsis

The reaction of [di(acyloxy)iodo]benzene with secondary phosphine oxides or H-phosphinates in the presence of primary or secondary amines allows one to obtain phosphinic or phosphonic acids amides in the one-pot process. We take advantage of the strong acylating system DAIB/R 2 P(O)H to phosphinylation of amines. However, the reaction mechanism is multipathway and causes yields of phosphinic or phosphonic acids amides to be moderate. When the concentration of amines is low, the intermolecular process plays a main role leading to the formation of carboxylic amides through mixed phosphoric-carboxylic anhydride, and also in the low concentration of amines, tetrahydrofuran effectively competes with the amines in the nucleophilic attack on the acylating intermediates.