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DOI: 10.1055/s-2007-983798
Regioselective Bipyrrole Coupling of Pyrroles and 3-Substituted Pyrroles Using Phenyliodine(III) Bis(trifluoroacetate)
Publikationsverlauf
Publikationsdatum:
12. Juli 2007 (online)

Abstract
A series of electron-rich bipyrroles were prepared by the regioselective, phenyliodine(III) bis(trifluoroacetate) (PIFA) induced oxidative coupling of pyrroles in the presence of bromotrimethylsilane. Using pyrrole and 3,4-disubstituted pyrroles gave exclusively 2,2′-linked bipyrroles without the formation of other bipyrrole regioisomers. The 3-alkyl- or 3-aryl-substituted pyrroles gave unsymmetrical H-T dimers in high yields as the major isolable α-linked bipyrrole products over the symmetrical H-H dimers. The nature of the N-substituent significantly influences the regioselectivity of the reaction, thus regiocontrolled bipyrrole coupling of N-phenyl- and N-benzyl-substituted pyrroles gave 2,3′-bipyrroles.
Key words
bipyrrole - hypervalent iodine compound - bromotrimethylsilane - oxidative coupling - Lewis acid - regioselectivity
- 1a
Kleemann A.Engel J.Kutscher B.Reichert D. Pharmaceutical Substances: Synthesis, Patents, Applications 4th ed.: Georg Thieme; Stuttgart: 2001. - 1b
Korostova SE.Mikhaleva AI.Trofimov BA. Russ. Chem. Rev. 1999, 68: 459 - 2a
Sessler JL.Camiolo S.Gale PA. Coord. Chem. Rev. 2003, 240: 17 - 2b
Sessler JL.Seidel D. Angew. Chem. Int. Ed. 2003, 42: 5134 - 3a
Rapoport H.Castagnoli N. J. Am. Chem. Soc. 1962, 84: 2178 - 3b
Bordner J.Rapoport H. J. Org. Chem. 1965, 30: 3824 - 3c
Brown D.Griffiths D.Rider ME.Smith RC. J. Chem. Soc., Perkin Trans. 1 1986, 455 - 3d
Benincori T.Brenna E.Sannicolò F.Zotti G.Zecchin S.Schiavon G.Gatti C.Frigerio G. Chem. Mater. 2000, 12: 1480 - Recent reports:
- 4a
Shevchuk VS.Davis JM.Sessler JL. Tetrahedron Lett. 2001, 42: 2447 - 4b
Merz A.Anikin S.Lieser B.Heinze J.John H. Chem. Eur. J. 2003, 9: 449 - 4c
Yu M.Pantos GD.Sessler JL.Pagenkopf BL. Org. Lett. 2004, 6: 1057 - 4d
Jolicoeur B.Lubell WD. Org. Lett. 2006, 8: 6107 ; and references cited therein - 5a
Itahara T. J. Chem. Soc., Chem. Commun. 1980, 49 - 5b
Itahara T. J. Org. Chem. 1985, 50: 5272 - 5c
Boger DL.Patel M. Tetrahedron Lett. 1987, 28: 2499 - 6a
Sessler JL.Tomat E.Lynch VM. Chem. Commun. 2006, 4486 - 6b
Lisowski J.Sessler JL.Lynch V. Inorg. Chem. 1995, 34: 3567 - 6c
Lausmann M.Zimmer I.Lex J.Lueken H.Wieghardt K.Vogel E. Angew. Chem., Int. Ed. Engl. 1994, 33: 736 - 6d
Electronic Materials: The Oligomer Approach
Müllen K.Wegner G. Wiley-VCH; Weinheim: 1998. - 6e
Baughman RH. Science 2005, 308: 63 - 7a
Tohma H.Morioka H.Takizawa S.Arisawa M.Kita Y. Tetrahedron 2001, 57: 345 ; and references therein - 7b
Tohma H.Iwata M.Maegawa T.Kita Y. Tetrahedron Lett. 2002, 43: 9241 - 7c
Dohi T.Morimoto K.Kiyono Y.Maruyama A.Tohma H.Kita Y. Chem. Commun. 2005, 2930 - 8
Kita Y.Tohma H.Hatanaka K.Takada T.Fujita S.Mitoh S.Sakurai H.Oka S. J. Am. Chem. Soc. 1994, 116: 3684 - 9
Dohi T.Morimoto K.Maruyama A.Kita Y. Org. Lett. 2006, 8: 2007 - 10
Farnier M.Soth S.Fournari P. Can. J. Chem. 1976, 54: 1083 - For recent reviews see:
- 11a
Stang PJ.Zhdankin VV. Chem. Rev. 1996, 96: 1123 - 11b
Kita Y.Takada T.Tohma H. Pure Appl. Chem. 1996, 68: 627 - 11c
Varvoglis A. Hypervalent Iodine in Organic Synthesis Academic Press; San Diego: 1997. - 11d
Kirschning A. Eur. J. Org. Chem. 1998, 2267 - 11e
Ochiai M. In Chemistry in Hypervalent CompoundsAkiba K. Wiley-VCH; New York: 1999. Chap. 12. - 11f
Zhdankin VV.Stang PJ. Chem. Rev. 2002, 102: 2523 - 11g
Hypervalent Iodine Chemistry
Wirth T. Springer-Verlag; Berlin: 2003. - 11h
Moriarty RM. J. Org. Chem. 2005, 70: 2893 - 11i
Wirth T. Angew. Chem. Int. Ed. 2005, 44: 3656 - Utility of the head-to-tail dimers of heteroaromatic compounds, see:
- 12a
Roncali J. Chem. Rev. 1992, 92: 711 - 12b
McCullough RD. Adv. Mater. (Weinheim, Ger.) 1998, 10: 93 - 12c
G atti C.Frigerio G.Benincori T.Brenna E.Sannicolò F.Zotti G.Zecchin S.Schiavon F. Chem. Mater. 2000, 12: 1490 - For example:
- 13a
Candy CF.Jones RA.Wright PH. J. Chem. Soc. C 1970, 2563 - 13b
Gilow HM.Burton DE. J. Org. Chem. 1981, 46: 2221 - 13c
Muchowski JM.Solas DR. Tetrahedron Lett. 1983, 24: 3455 - 14
White JD.Caravatti G.Kline TB.Edstrom E.Rice KC.Brossi A. Tetrahedron 1983, 39: 2393 - 15a
Franck B.Nonn A.Fuchs K.Gosmann M. Liebigs Ann. Chem. 1994, 503 - 15b
Finikova OS.Cheprakov AV.Beletskaya IP.Carroll PJ.Vinogradov SA. J. Org. Chem. 2004, 69: 522 - 15c
Zelikin A.Shastri VR.Langer R. J. Org. Chem. 1999, 64: 3379 - 15d
Smith ND.Huang D.Cosford NDP. Org. Lett. 2002, 4: 3537 - 15e
Dohi T.Morimoto K.Kiyono Y.Tohma H.Kita Y. Org. Lett. 2005, 7: 537