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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 14
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Original Articles

Efficient Procedure for the Preparation of 2-Bromofuran and Its Application in the Synthesis of 2-Arylfurans

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Pages 2138-2146 | Received 06 May 2009, Published online: 17 Jun 2010

REFERENCES

  • For selected examples of our recent studies of Ru-catalyzed [2 + 2] cycloadditions of bicyclic alkenes and alkynes, see (a) Villeneuve , K. ; Tam , W. Asymmetric induction in ruthenium-catalyzed [2 + 2] cycloadditions between bicyclic alkenes and chiral acetylenic acylsultam . Angew. Chem. Int. Ed . 2004 , 43 , 610 – 613 ; (b) Burton , R. R. ; Tam , W. Ruthenium-catalyzed [2 + 2] cycloadditions between C1-substituted 7-oxanorbornadienes and alkynes . Tetrahedron Lett. 2006 , 47 , 7185 – 7189 ; (c) Burton , R. R. ; Tam , W. Study on the reactivity of oxabicyclic alkenes in ruthenium-catalyzed [2 + 2] cycloadditions . J. Org. Chem. 2007 , 72 , 7333 – 7336 ; (d) Allen , A. ; Villeneuve , K. ; Cockburn , N. ; Fatila , E. ; Riddell , N. ; Tam , W. Alkynyl halides in ruthenium(II)-catalyzed [2 + 2] cycloadditions of bicyclic alkenes . Eur. J. Org. Chem . 2008 , 4178 – 4192 .
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  • Villeneuve , K. ; Tam , W. Ruthenium-catalyzed isomerization of oxa/azabicyclic alkenes: An expedient route for the synthesis of 1,2-naphthalene oxides and imines . J. Am. Chem. Soc. 2006 , 128 , 3514 – 3515 .
  • Allen , A. ; Le Marquand , P. ; Burton , R. ; Villeneuve , K. ; Tam , W. Rhodium-catalyzed asymmetric cyclodimerization of oxabenzonorbornadienes and azabenzonorbornadienes: Scope and limitations. J. Org. Chem. 2007, 72, 7849–7857.
  • (a) Jclopp , A. H. ; Wright , G. F. The action of bromocyanogen of furan . J. Org. Chem. 1939 , 4 , 142 – 149 ; (b) Fuchs , B. ; Belsky , Y. ; Tartakovsky , E. ; Zizuashvili , J. ; Weinman , S. Novel bromination reagents: Electrophilic aromatic bromination by hexabromocyclopentadiene . J. Chem. Soc., Chem. Commun . 1982 , 778 – 779 ; (c) Lukevicss , E. ; Ignatovich , L. ; Goldberg , Y. ; Polyak , F. ; Gaukhman , A. ; Rozite , S. ; Popelis , J. Reactions of trialkyl(2-furyl)germanes with electrophilic reagents . J. Organomet. Chem. 1988 , 348 , 11 – 23 ; (d) Verkruijsse , H. D. ; Keegstra , M. A. ; Brandsma , L. A high-yield preparative-scale method for 2-bromofuran . Synth. Commun. 1989 , 19 , 1047 – 1049 ; (e) Keegstra , M. A. ; Klomp , A. J. ; Brandsma , L. Convenient synthetic procedures for 2-bromofuran and 2,5-dibromofuran . Synth. Commun. 1990 , 20 , 3371 – 3374 ; (f) Goldberg , Y. ; Alper , H. Electrophilic halogenation of aromatics and heteroaromatics with N-halosuccinimides in a solid/liquid system using an H+ ion exchanger or ultrasonic irradiation . J. Mol. Catal. 1994 , 88 , 377 – 383 ; (g) Gupta , N. ; Kad , G. L. ; Singh , V. ; Singh , J. Regioselective photochemical and microwave mediated monobromination of aromatic compounds using 2,4,4,6-tetrabromo-2,5-cyclohexadienone . Synth. Commun . 2007 , 37 , 3421 – 3428 .

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