13780-95-5Relevant academic research and scientific papers
Improved procedure for the bimolecular oxidative amidation of phenols
Liang, Huan,Ciufolini, Marco A.
, p. 4299 - 4301 (2008)
(Chemical Equation Presented) Trifluoroacetic acid (TFA) is an effective promoter of the bimolecular Ritter-like oxidative amidation of 4-substituted phenols induced by PhI(OAc)2 in MeCN. This suppresses the need for fluoroalcohol cosolvents, i
Synthetic aspects of the oxidative amidation of phenols
Liang, Huan,Ciufolini, Marco A.
experimental part, p. 5884 - 5892 (2010/09/09)
The oxidative amidation of phenols effects the conversion of appropriately substituted phenols into 4-amidodienones ('para-oxidative amidation') or 2-amidodienones ('ortho-oxidative amidation') by the action of hypervalent iodine reagents. The reagent, (diacetoxyiodo)benzene ('DIB') is especially effective in these transformations. This paper focuses on techniques for the desymmetrization of the dienoes thus obtained, leading to the stereocontrolled creation of N-substituted spiro carbons. The methodology creates new opportunities in alkaloid synthesis, as apparent from a number of examples. DIB=PhI(OAc)2. The reaction may be carried out in the intra- or the intermolecular mode.
