Oxidative Bromination of Aromatic Compounds Using O-Iodoxybenzoic Acid with Tetraethylammonium Bromide

REFERENCES

• Diederich , F. ; Stang , P. J. Metal-Catalyzed Cross-Coupling Reactions ; John Wiley & Sons : New York , 1997 .
   Google Scholar
• De la Mare , P. B. Electrophilic Halogenation ; Cambridge University Press : Cambridge , 1976 .
   Google Scholar
• Budavari , S. ; O'Neil , M. J. ; Smith , A. ; Heckelman , P. E. ; Kinneary , J. F. The Merck Index, , 12th ed. ; Merck : Rahway , New Jersey , USA , 1996 .
   Google Scholar
• (a) Park , M. Y. ; Yang , S. G. ; Jadhav , V. ; Kim , Y. H. Practical and regioselective brominations of aromatic compounds using tetrabutylammonium peroxydisulfate . Tetrahedron Lett. 2004 , 45 , 4887 , and references cited therein; (b) Roy , S. C. ; Guin , C. ; Rana , K. K. ; Maiti , G. An efficient chemo and regioselective oxidative nuclear bromination of activated aromatic compounds using lithium bromide and ceric ammonium nitrate . Tetrahedron Lett. 2001 , 42 6941 .
   Web of Science ®Google Scholar
• Majetich , G. ; Hicks , R. ; Reister , S. Electrophilic aromatic bromination using bromodimethylsulfonium bromide generated in situ . J. Org. Chem. 1997 , 62 , 4321 .
   PubMed Web of Science ®Google Scholar
• (a) Braddock , O. C. ; Cansell , G. ; Hermitage , S. A. (Diacetoxyiodo)benzene-lithium bromide as a convenient electrophilic Br+ source . Synlett 2004 , 3 , 461 ; (b) Kim , D. K. ; Chung , W. J. ; Lee , Y. S. Simple bromination of activated arenes by IBX amide resin and tetraethylammoniumbromide . Synlett 2005 , 2 , 279 .
   Web of Science ®Google Scholar
• (a) Bhalerao , D. S. ; Mahajan , U. S. ; Chaudhari , K. H. ; Akamanchi , K. G. o-Iodoxybenzoic acid–and tetraethylammonium bromide–mediated oxidative transformation of primary carboxamides to one-carbon dehomologated nitriles . J. Org. Chem. 2007 , 72 , 662 , and references cited therein .
   PubMed Web of Science ®Google Scholar
• Keegstra , M. A. ; Brandsma , L. Convenient high-yield procedures for 2-bromothiophene and 2,5-dibromothiophene . Synthesis 1988 , 890 .
   Web of Science ®Google Scholar
• Zhang , D. ; Llorente , I. ; Liebskind , L. S. Versatile synthesis of dihydroquinolines and quinones using cyclobutenediones: Construction of the pyridoacridine ring system . J.Org. Chem. 1997 , 62 , 4330 .
   PubMed Web of Science ®Google Scholar
• Horner , L. ; Einkrlmsnn , E. ; Knapp , K. H. ; Ludwig , W. The course of substitution, XIV: The reaction of tertiary amines with N-bromosuccinimide and lead tetraacetate . Chem. Ber. 1959 , 92 , 288 ; Chem. Abstr. 53, 11277i .
   Google Scholar
• Kobayashi , K. ; Tokimatsu , J. ; Maedo , K. ; Morikawa , O. ; Konishi , H. New short synthesis of arylnaphthofuranone lignans based on reactions of o-aroylbenzyllithiums with furan-2(5H)-one . J. Chem. Soc., Perkin Trans. 1 1995 , 23 , 3013 .
   Google Scholar