RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2011(2): 207-209
DOI: 10.1055/s-0030-1258350
DOI: 10.1055/s-0030-1258350
SHORTPAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
An Efficient and Regioselective Monobromination of Electron-Rich Aromatic Compounds Using Catalytic Hypervalent Iodine(III) Reagent
Weitere Informationen
Received
24 September 2010
Publikationsdatum:
03. Dezember 2010 (online)
Publikationsverlauf
Publikationsdatum:
03. Dezember 2010 (online)
Abstract
An efficient and regioselective monobromination of electron-rich aromatic compounds is reported in which iodobenzene is used as the recyclable catalyst in combination with m-chloroperbenzoic acid as the terminal oxidant. The bromination of electron-rich aromatic compounds with lithium bromide was fast in tetrahydrofuran at room temperature, providing regioselective monobrominated products in good yields.
Key words
monobromination - hypervalent iodine reagent - catalytic oxidation
-
1a
Diederich F.Stang PJ. Metal Catalyzed Cross Coupling Reactions Wiely-VCH; Weinheim: 1998. -
1b
Miyaura N.Yamada K.Suginome H.Suzuki A. J. Am. Chem. Soc. 1985, 107: 972 -
1c
Taylor R. Electrophilic Aromatic Substitution Wiley; New York: 1990. -
1d
De La Mare PBD. Electrophilic Halogenation Cambridge University Press; Cambridge: 1976. Chap. 5. -
2a
Dieter RK.Nice LE.Velu SE. Tetrahedron Lett. 1996, 37: 2377 -
2b
Nair V.Panicker SB.Augstine A.George TG.Thomas S.Vairamani M. Tetrahedron 2001, 57: 7417 -
2c
Dewkar KG.Narina VS.Sudalai A. Org. Lett. 2003, 5: 4501 -
2d
Ye C.Shreeve MJ. J. Org. Chem. 2004, 69: 8561 -
2e
Kumar MA.Rohitha CN.Kulkarni SJ.Narender N. Synlett 2010, 1629 -
3a
Khan AT.Goswami P.Choudhury LH. Tetrahedron Lett. 2006, 47: 2751 -
3b
Moriuchi T.Yamaguchi M.Kikushima K.Hirao T. Tetrahedron Lett. 2007, 48: 2667 -
3c
Greb M.Hartung J.Kohler F.Spehar K.Kluge R.Csuk R. Eur. J. Org. Chem. 2004, 3799 -
3d
Nica S.Pohlmann A.Plass W. Eur. J. Inorg. Chem. 2005, 2032 -
3e
Crans DC.Smee JJ.Gaidamauskas G.Yang L. Chem. Rev. 2004, 104: 849 -
3f
Zhang G.Liu R.Xu Q.Ma L.Liang X. Adv. Synth. Catal. 2006, 348: 862 -
3g
Podgorsek A.Eissen M.Fleckenstein J.Stavber S.Zupan M.Iskra J. Green Chem. 2009, 11: 120 -
3h
Kikushima K.Moriuchi T.Hirao T. Tetrahedron Lett. 2010, 51: 340 -
3i
Yang L.-J.Lu Z.Stahl SS. Chem. Commun. 2009, 6460 -
4a
Zhang Y.Shibatomi K.Yamamoto H. Synlett 2005, 2837 -
4b
Yadav JS.Reddy BVS.Reddy PSR.Basak AK.Narsaiah AV. Adv. Synth. Catal. 2004, 346: 77 -
4c
Ganguly NC.De S.Dutta P. Synthesis 2005, 1103 -
4d
Kalyani D.Dick AR.Anani WQ.Sanford MS. Org. Lett. 2006, 8: 2523 -
4e
Kalyani D.Dick AR.Anani WQ.Sanford MS. Tetrahedron 2006, 62: 11483 -
4f
Mo F.-Y.Yan JM.Qiu D.Li F.Zhang Y.Wang J.-B. Angew. Chem. Int. Ed. 2010, 49: 2028 -
5a
Varvoglis A. Tetrahedron 1997, 53: 1179 -
5b
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 -
5c
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 -
5d
Kirschning A. Eur. J. Org. Chem. 1998, 11: 2267 -
5e
Ochiai M. J. Organomet. Chem. 2000, 611: 494 -
5f
Okuyama T. Acc. Chem. Res. 2002, 35: 12 -
5g
Zhdankin VV.Stang PJ. Tetrahedron 1998, 54: 10927 -
5h
Grushin VV. Chem. Soc. Rev. 2000, 29: 315 -
6a
Bovonsombat P.Angara GJ.McNelis E. Synlett 1992, 131 -
6b
Bovonsombat P.Elsa D.McNelis E. Tetrahedron Lett. 1994, 35: 2841 -
6c
Braddock DC.Cansell G.Hermitage SA. Synlett 2004, 461 -
7a
Dohi T.Kita Y. Kagaku 2006, 61: 68 -
7b
Richardson RD.Wirth T. Angew. Chem. Int. Ed. 2006, 45: 4402 -
7c
Dohi T.Minamitsuji Y.Maruyama A.Hirose S.Kita Y. Org. Lett. 2008, 10: 3559 -
7d
Ochiai M. Chem. Rec. 2007, 7: 13 -
7e
Uyanik M.Ishihara K. Chem. Commun. 2009, 2086 -
7f
Dohi T.Kita Y. Chem. Commun. 2009, 2073 -
7g
Liu H.-G.Tan C.-H. Tetrahedron Lett. 2007, 48: 8220 - 8
Zhou Z.-S.He X.-H. Tetrahedron Lett. 2010, 51: 2480 - 9
Srebnik M.Mechoulam R.Yona I. J. Chem. Soc., Perkin Trans. 1 1987, 1423