Abstract
The combination of PPh(3)/I(2) has been shown to be effective for conversion of a range of carboxylic acids to 2°, 3°, and Weinreb amides. Simplification of the procedure was possible with the use of polymer-supported PPh(3)/I(2). Weinreb amides produced via the use of polymer-supported PPh(3) could be filtered through a short silica gel plug and used in further transformations. Thus, use of polymer-supported PPh(3) offers potential applicability to diversity-oriented reactions. Formal total syntheses of apocynin and pratosine, as well as syntheses of anhydrolychorinone and hippadine, have been achieved via the use of this amide-forming method. An attempt has been made to gain insight into this reaction.