Journal
SYNTHESIS-STUTTGART
Volume 52, Issue 21, Pages 3253-3262Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707174
Keywords
amide bond formation; organophosphorus catalyst; dehydration; carboxylic acids; amines
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The atom-efficient formation of amide bonds has emerged as a top-priority research field in organic synthesis, as amide bonds constitute the backbones of proteins and represent an important structural motif in drug molecules. Currently, the increasing demand for novel discoveries in this field has focused substantial attention on this challenging subject. Herein, the degradable 1,3,5-triazo-2,4,6-triphosphorine (TAP) motif is presented as a new condensation system for the dehydrative formation of amide bonds between diverse combinations of aromatic carboxylic acids and amines. The underlying reaction mechanism was investigated, and potential catalyst intermediates were characterized using(31)P NMR spectroscopy and ESI mass spectrometry.
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