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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 5
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Original Articles

Mild, Efficient, and Regioselective Monobromination of Arylamines and Phenols Using [BBIm]Br3 as a New Reagent

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Pages 647-653 | Received 05 Feb 2009, Published online: 04 Feb 2010

REFERENCES

  • (a) Kuroboshi , M. ; Waki , Y. ; Tanaka , H. Palladium-catalyzed tetrakis(dimethylamino)ethylene-promoted reductive coupling of aryl halides . J. Org. Chem. 2003 , 68 , 3938 ; (b) Qingwei , Y. ; Elizabeth , P. K. ; Zhi , Y. Ligand-free Heck reaction: Pd(OAc)2 as an active catalyst revisited . J. Org. Chem. 2003 , 68 , 7528 .
  • (a) Gao , C. ; Tao , X. ; Qian , Y. ; Huang , J. A highly efficient catalytic system for cross-coupling of aryl chlorides and bromides with malononitrile anion by palladium carbene complexes . Chem. Commun. 2003 , 12 , 1444 ; (b) Euzenat , L. ; Horhant , D. ; Ribourdouille , Y. ; Duriez , C. ; Alcaraz , G. ; Vaultier , M. Monomeric (dialkylamino)boranes: A new and efficient boron source in palladium-catalyzed C-B bond formation with aryl halides . Chem. Commun. 2003 , 18 , 2280 .
  • Onaka , M. ; Izumi , Y. Selective monobromination of aniline derivatives by use of bromine adsorbed on zeolite 5A . Chem. Lett. 1984 , 13 , 2007 .
  • Larock , R. C. Comprehensive Organic Transformation ; VCH : New York , 1989 ; p. 315 .
  • Dewkar , G. K. ; Narina , S. V. ; Sudalai , A. NaIO4-mediated selective oxidative halogenation of alkenes and aromatics using alkali metal halides . Org. Lett. 2003 , 5 , 4501 .
  • Paul , V. ; Sudalai , A. ; Daniel , T. ; Srinivasan , K. V. Regioselective bromination of activated aromatic substrates with N-bromosuccinimide over HZSM-5 . Tetrahedron Lett. 1994 , 35 , 7055 .
  • Buckles , R. E. ; Popov , A. I. ; Zelezny , W. F. ; Smith , R. J. Spectrophotometric study of tetrabutylammonium tribromide . J. Am. Chem. Soc. 1951 , 73 , 4525 .
  • Muathen , H. A. 1,8-Diazabicyclo[5.4.0]undec-7-ene hydrobromide perbromide: A new, mild, stable, brominating agent for aromatic compounds . J. Org. Chem. 1992 , 57 , 2740 .
  • Cerichelli , G. ; Luchetti , L. ; Mancini , G. Surfactant control of the ortho/para ratio in the bromination of anilines . Tetrahedron Lett. 1989 , 30 , 6209 .
  • Reeves , W. P. ; King , R. M. A convenient method for bromination of aromatic amines . Synth. Commun. 1993 , 23 , 855 .
  • 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.
  • Srivastava , S. K. ; Chauhan , P. M. S. ; Bhaduri , A. P. Novel site-specific one–step bromination of substituted benzenes . Chem. Commun. 1996 , 23 , 2679 .
  • Chiappe , C. ; Capraro , D. ; Conte , V. ; Pieraccini , D. Stereoselective halogenations of alkenes and alkynes in ionic liquids . Org. Lett. 2001 , 3 , 1061 .
  • Horvath , I. T. ; Anastas , P. T. Innovations and green chemistry . Chem. Rev. 2007 , 107 , 2169 .
  • (a) Ranu , B. C. ; Banerjee , S. J. Ionic liquid as reagent: A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst and solvent-free conditions . J. Org. Chem. 2005 , 70 , 4517 ; (b) Davis , J. H. Task-specific ionic liquids . Chem. Lett. 2004 , 33 , 1072 ; (c) Earle , M. J. ; Katdare , S. P. ; Seddon , K. R. Paradigm confirmed: The first use of ionic liquids to dramatically influence the outcome of chemical reactions . Org. Lett. 2004 , 6 , 707 .
  • (a) Iranpoor , N. ; Firouzabadi , H. ; Azadi , R. A new diphenylphosphinite ionic liquid (IL-OPPh2) as reagent and solvent for highly selective bromination, thiocyanation, or isothiocyanation of alcohols and trimethylsilyl and tetrahydropyranyl ethers . Tetrahedron Lett. 2006 , 47 , 5531 ; (b) Le , Z. G. ; Chen , Z. C. ; Hu , Y. ; Zheng , Q. G. [Bmim]Br3 as a new reagent for regioselective monobromination of arylamines under solvent-free conditions . Synthesis 2004 , 17 , 2809 ; (c) Salazar , J. ; Dorta , R. Pentylpyridinium tribromide: A vapor pressure free room temperature ionic liquid analogue of bromine . Synlett 2004 , 7 , 1318 ; (d) Chiappe , C. ; Leandri , E. ; Pieraccini , D. Highly efficient bromination of aromatic compounds using 3-methylimidazolium tribromide as reagent/solvent . Chem. Commun. 2004 , 22 , 2536 .
  • Borikar , S. P. ; Daniel , T. ; Paul , V. An efficient, rapid, and regioselective bromination of anilines and phenols with 1-butyl-3-methylpyridinium tribromide as a new reagent/solvent under mild conditions . Tetrahedron Lett. 2009 , 50 , 1007 .

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