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Review
. 2007 Jul;36(7):1173-93.
doi: 10.1039/b606984n. Epub 2007 Mar 5.

Direct transition metal-catalyzed functionalization of heteroaromatic compounds

Ilya V Seregin  1 , Vladimir Gevorgyan
Affiliations
Review

Direct transition metal-catalyzed functionalization of heteroaromatic compounds

Ilya V Seregin et al. Chem Soc Rev. 2007 Jul.

Abstract

During the last two decades there has been considerable growth in the development of catalytic reactions capable of activating unreactive C-H bonds. These methods allow for the synthesis of complex molecules from easily available and cheaper precursors in a fewer number of steps. Naturally, the development of C-H activation methods for direct functionalization of heterocyclic molecules, invaluable building blocks for pharmaceutical and synthetic chemistry and material science, has received substantial attention as well. This critical review summarizes the progress made in this field until November 2006 (117 references).

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Figures

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Proposed mechanisms for Pd-catalyzed arylation of electron-rich hetroaromatic compounds.
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Attempts to perform cascade Heck reaction on indolizine.
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Attempts to perform reductive Heck reaction.
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Arylation of 6-carboethoxyindolizine.
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Possible C–H activation mechanism: isotope effect study.
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Possible pathways for C-2 and C-3 arylation of indoles.
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Kinetic isotope effect in the phenylation of C-2 and C-3 positions of indole.
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Condition-dependent Heck vs electrophilic arylation.
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Competitive experiment and kinetic studies of pyridine oxide arylation.
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Generalized mechanistic rationale for intramolecular alkylation of indole with olefins.
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References

    1. For reviews on C–H activation, see: Godula K, Sames D. Science. 2006;312:67. Jia CG, Kitamura T, Fujiwara Y. Acc. Chem. Res. 2001;34:844. Ritleng V, Sirlin C, Pfeffer M. Chem. Rev. 2002;102:1731. Kakiuchi F, Murai S. Acc. Chem. Res. 2002;35:826.

    1. Ames DE, Bull D. Tetrahedron. 1982;38:383.
    1. Pivsa-Art S, Satoh T, Kawamura Y, Miura M, Nomura M. Bull. Chem. Soc. Jpn. 1998;71:467.
    1. Okazawa T, Satoh T, Miura M, Nomura M. J. Am. Chem. Soc. 2002;124:5286. - PubMed
    1. Glover B, Harvey KA, Liu B, Sharp MJ, Tymoschenko M. Org. Lett. 2003;5:301. - PubMed

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