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Simple Synthesis of Amides and Weinreb Amides via Use of PPh 3 or Polymer-Supported PPh 3 and Iodine

The combination of PPh /I 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 /I . Weinreb amides produced via the use of polymer-supported PPh could be filtered...

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Bibliographic Details
Published in:European journal of organic chemistry 2010-05, Vol.2010 (14)
Main Authors: Kumar, Amit, Akula, Hari Kiran, Lakshman, Mahesh K
Format: Article
Language:English
Online Access:Get full text
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Summary:The combination of PPh /I 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 /I . Weinreb amides produced via the use of polymer-supported PPh could be filtered through a short silica gel plug and used in further transformations. Thus, use of polymer-supported PPh 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.
ISSN:1434-193X