Improved procedure for the bimolecular oxidative amidation of phenols

Journal of Organic Chemistry

Volumn 73, Issue 11, 2008, Pages 4299-4301

  Liang, Huan ^a   Ciufolini, Marco A ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS;

4-SUBSTITUTED PHENOLS; AMIDATION; CHEMICAL EQUATIONS; TRIFLUOROACETIC ACID (TFA);

PHENOLS;

ALCOHOL DERIVATIVE; PHENOL DERIVATIVE; TRIFLUOROACETIC ACID;

AMIDATION; ARTICLE; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS;

AMIDES; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; PHENOLS;

EID: 44949129833     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800267q     Document Type: Article

References (36)

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28. 3) may form under these conditions.
29. Many compounds of the type 2 are water-soluble, a property that complicates aqueous workups.
30. While most dienones 2 are sensitive to prolonged exposure to excess TFA (ref 1), the small amounts of TFA that accumulate in the solution during concentration of these reaction mixtures have little adverse effect on compounds 2 if R is a group possessing poor migratory aptitude in the dienone-phenol rearrangement, e.g., a primary (cf. 4b,c,e,j) or an electronically deactivated (4a) alkyl substituent. Dienones incorporating secondary (cf. 4d) or tertiary C-4 alkyls (cf. Scheme 3) are progressively more prone to undergo dienone-phenol rearrangement.
31. A series of reactions were run at 15-20°C intervals within this range.
32. The solvent may be recovered from the rotary evaporator and directly reused.
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36. Experimental protocols are provided as Supporting Information.