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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 19
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Original Articles

Electrophilic Bromination of Alkenes, Alkynes, and Aromatic Amines with Iodic Acid/Potassium Bromide Under Mild Conditions

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Pages 2954-2962 | Received 22 Aug 2009, Published online: 25 Aug 2010

REFERENCES

  • House , H. O. In Modern Synthetic Reactions ; W. A. Benjamin (Ed.); Inc. : Menlo Park , CA , 1972 ; p. 422 .
  • Liu , Y. H. ; Zhou , S. L. Electrophilic cyclization of 2-(1-alkynyl)-2-alken-1-ones using the I2/K3PO4 system: An efficient synthesis of highly substituted iodofurans . Org. Lett. 2005 , 7 , 4609 – 4611 .
  • Johnsson , R. ; Meijer , A. ; Ellervik , U. Mild and efficient direct aromatic iodination . Tetrahedron 2005 , 61 , 11657 – 11663 .
  • Ranu , B. C. ; Guchhait , S. K. ; Sarkar , A. Stereoselective debromination of aryl-substituted vic-dibromide with indium metal . Chem. Commun. 1998 , 2113 – 2114 .
  • Rieke , R. D. ; Sell , M. S. In Handbook of Grignard Reagents ; G. S. Silverman , P. E. M. Rakita (Eds.); Dekker : New York , 1996 ; p. 527 .
  • Wakefield , B. J. The Chemistry of Organolithium Compounds ; Pergamon Press : Oxford , 1976 .
  • Davis , S. G. Organotransition Metal Chemistry: Applications to Organic Synthesis ; Pergamon Press : Oxford , 1982 .
  • Cannon , K. C. ; Krow , G. R. Handbook of Grignard Reagents ; Dekker : New York , 1996 .
  • Still , J. K. Palladium-catalyzed coupling of organotin reagents with organic electrophiles . Pure Appl. Chem. 1985 , 57 , 1771 – 1780 .
  • Miyaura , N. ; Suzuki , A. Palladium-catalyzed cross-coupling reactions of organoboron compounds . Chem. Rev. 1995 , 95 , 2457 – 2843 .
  • Beletskaya , I. P. ; Cheprakov , A. V. Heck reaction as a sharpening stone of palladium catalysis . Chem. Rev. 2000 , 100 , 3009 – 3066 .
  • Cabri , W. ; Candiani , I. Recent developments and new perspectives in the Heck reaction . Acc. Chem. Res. 1995 , 28 , 2 – 7 .
  • Butler , A. ; Walker , J. V. Marine haloperoxidases . Chem. Rev. 1993 , 93 , 1937 – 1944 .
  • Bora , U. ; Bose , G. ; Chaudhuri , M. K. ; Dhar , S. S. ; Gopinath , R. ; Khan , A. T. ; Patel , B. K. Regioselective bromination of organic substrates by tetrabutylammonium bromide promoted by V2O5-H2O2: An environmentally favorable synthetic protocol . Org. Lett. 2000 , 2 , 247 – 249 .
  • Becker , H. G. O. In Organikum: Organisch-chemisches Grundpraktikum ; Wiley-VCH : Weinheim , 2001 ; p. 299 .
  • Ryu , I. ; Matsubara , H. ; Yasuda , S. ; Nakamura , H. ; Curran , D. P. Phase-vanishing reactions that use fluorous media as a phase screen: Facile, controlled bromination of alkenes by dibromine and dealkylation of aromatic ethers by boron tribromide . J. Am. Chem. Soc. 2002 , 124 , 12946 – 12947 .
  • Chiappe , C. ; Capraro , D. ; Conte , V. ; Pieraccini , D. Stereoselective halogenations of alkenes and alkynes in ionic liquids . Org. Lett. 2001 , 3 , 1061 – 1063 .
  • Larock , R. C. In Comprehensive Organic Transformation: A Guide to Functional Group Preparation ; Wiley-VCH : New York , 1999 ; p. 629 .
  • Dalton , D. R. ; Dutta , V. P. ; Jones , D. C. Bromohydrin formation in dimethylsulfoxide . J. Am. Chem. Soc. 1968 , 90 , 5498 – 5502 .
  • Eissen , M. ; Lenoir , D. Electrophilic bromination of alkenes: Environmental, health, and safety aspects of new alternative method . Chem. Eur. J. 2008 , 14 , 9830 – 9841 .
  • Gallou , F. ; Reeves , J. T. ; Tan , Z. L. ; Songa , J. H. J. ; Yee , N. K. ; Campbell , S. ; Jones , P. J. ; Senanayake , C. H. Regioselective halogenation of 6-azaindoles: Efficient synthesis of 3-halo-2,3-disubstituted-6-azaindole derivatives . Synlett. 2005 , 2400 – 2402 .
  • Moghaddam , F. M. ; Boeini , H. Z. Oxidative cyclization of thiobenzanilides to benzothiazoles using N-benzyl-DABCO tribromide under mild conditions . Synlett. 2005 , 1612 – 1614 .
  • de Almeida , L. S. ; Esteves , P. M. ; de Mattos , M. C. S. Tribromoisocyanuric acid: A new reagent for regioselective cobromination of alkenes. Synlett. 2006, 1515–1518.
  • de Almeida , L. S. ; Esteves , P. M. ; de Mattos , M. C. S. A new regioselective bromination of activated aromatic rings . Synthesis 2006 , 221 – 223 .
  • Zolfigol , M. A. ; Chehardoli , G. ; Salehzadeh , S. ; Adams , H. ; Ward , M. D. {[K.18-Crown-6]Br−3}(n): A unique tribromide-type and columnar nanotube-like structure for the oxidative coupling of thiols and bromination of some aromatic compounds . Tetrahedron Lett. 2007 , 48 , 7969 – 7973 .
  • de Almeida , L. S. ; Esteves , P. M. ; de Mattos , M. C. S. Efficient electrophilic cobromination of alkenes and bromination of activated arenes with bromodichloroisocyanuric acid under mild conditions . Synlett. 2007 , 1687 – 1690 .
  • Ying , T. K. ; Bao , W. L. ; Zhang , Y. M. Bromination of carbon–carbon double bonds involving oxidation of NaBr in an ionic liquid . J. Chem. Res., Synop. 2004 , 806 – 807 .
  • Das , B. ; Srinivas , Y. ; Sudhakar , C. ; Damodar , K. ; Narender , R. Efficient bromination of alkenes and alkynes using potassium bromide and diacetoxy iodobenzene . Synth. Commun. 2009 , 39 , 220 – 227 .
  • Moriuchi , T. ; Yamaguchi , M. ; Kikushima , K. ; Hirao , T. An efficient vanadium-catalyzed bromination reaction . Tetrahedron Lett. 2007 , 48 , 2667 – 2670 .
  • Nair , V. ; Panicker , S. B. ; Augustine , A. ; George , T. G. ; Thomas , S. ; Vairamani , M. An efficient bromination of alkenes using cerium(IV) ammonium nitrate (CAN) and potassium bromide . Tetrahedron 2001 , 57 , 7417 – 7422 .
  • Joshi , A. V. ; Baidossi , M. ; Mukhopadhyay , S. ; Sasson , Y. Oxidative bromination of activated aromatic compounds using aqueous nitric acid as an oxidant . Org. Proc. Res. Dev. 2004 , 8 , 568 – 570 .
  • Muathen , H. A. Mild oxidative bromination of alkenes and alkynes with zinc bromide and lead tetraacetate . Synth. Commun. 2004 , 34 , 3545 – 3552 .
  • 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 – 1009 .
  • Pilli , R. A. ; Robello , L. G. Palladium-catalyzed double cross-coupling of E-vinylic dibromides with PhZnCl and the synthesis of tamoxifen . J. Braz. Chem. Soc. 2004 , 15 , 938 – 944 .
  • Barhate , N. B. ; Gajare , A. S. ; Wakharkar , R. D. ; Bedekar , A. V. Simple and practical halogenation of arenes, alkenes, and alkynes with hydrohalic acid/H2O2 (or TBHP) . Tetrahedron 1999 , 55 , 11127 – 11142 .
  • Smith , M. B. ; Guo , L. ; Okeyo , S. ; Stenzel , J. ; Yanella , J. ; LaChapelle , E. Regioselective one-pot bromination of aromatic amines . Org. Lett. 2002 , 4 , 2321 – 2323 .
  • Hashemi , M. M. ; Rahimi , A. ; Karimi-Jaberi , Z. ; Ahmadibeni , Y. A mild and efficient oxidation of benzylic alcohols without solvent using iodic acid supported on wet Montmorillonite K10 or silica gel under microwave irradiation . Acta Chim. Slov. 2005 , 52 , 86 – 87 .
  • Choghamarani , A. G. Iodic acid (HIO3) . Synlett. 2006 , 2347 – 2348 .
  • Hashemi , M. M. ; Naeimi , H. ; Shirazizadeh , F. ; Karimi-Jaberi , Z. Oxidation of α-hydroxy ketones to diketones by iodic acid supported on alumina . J. Chem. Res., Synop. 2006 , 345 – 345 .
  • Xu , L. A. ; Shu , H. ; Liu , Y. ; Zhang , S. H. ; Trudell , M. L. Oxidative cyclization of N-alkyl-o-methyl-arenesulfonamides to biologically important saccharin derivatives . Tetrahedron 2006 , 62 , 7902 – 7910 .
  • Zolfigol , M. A. ; Bagherzadeh , M. ; Niknam , K. ; Shirini , F. ; Mohammadpoor-Baltork , I. ; Choghamarani , A. G. ; Baghbanzadeh , M. Oxidation of 1,4-dihydropyridines under mild and heterogeneous conditions using solid acids . J. Iran. Chem. Soc. 2006 , 3 , 73 – 80 .
  • Zolfigol , M. A. ; Shirini , F. ; Chehardoli , G. ; Kolvari , E. A catalytic and transition-metal-free method for the chemoselective oxidation of alcohols to their corresponding carbonyl compounds using periodic acid or iodic acid in the presence of a catalytic amount of KBr. J. Mol. Catal. A: Chem. 2007, 265, 272–275.
  • Lulinski , P. ; Skulski , L. Iodination of both deactivated and activated arenes with sodium periodate or sodium iodate as the oxidants . Bull. Chem. Soc. Jpn. 2000 , 73 , 951 – 956 .
  • Hashemi , M. M. ; Bakhtiari , M. ; Karimi-Jaberi , Z. Efficient solvent-free deprotection of acetals and trimethylsilyl ethers with iodic acid on silica gel under microwave irradiation . Russ. J. Org. Chem. 2007 , 43 , 621 – 622 .

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