Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 14, Pages 2709-2715Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200901420
Keywords
Amides; Phosphanes; Supported reagents; Iodine; Synthetic methods
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Funding
- National Science Foundation (NSF) [CHE-0640417]
- National Institutes of Health (NIH) [5S06 GM008168-30]
- PSC CUNY
- Research Centers at Minority Institutions [NIH/NCRR/RCMI - G12 RR03060]
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The combination of PPh3/I-2 has been shown to be effective for the conversion of a range of carboxylic acids into secondary, tertiary, and Weinreb amides. Simplification of the procedure was possible with the use of polymer-supported PPh3/I-2. Weinreb amides produced with the use of polymer-supported PPh3 could be filtered through a short silica gel plug and used in further transformations. Thus, the use of polymer-supported PPh3 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 through the use of this amide-forming method. An attempt has been made to gain insight into this reaction.
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