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. 2004 Apr 1;6(7):1159-62.
doi: 10.1021/ol049866q.

Palladium-catalyzed arylation and heteroarylation of indolizines

Choul-Hong Park  1 , Victoria Ryabova, Ilya V Seregin, Anna W Sromek, Vladimir Gevorgyan
Affiliations

Palladium-catalyzed arylation and heteroarylation of indolizines

Choul-Hong Park et al. Org Lett. .

Abstract

A highly effective protocol for palladium-catalyzed selective arylation and heteroarylation of indolizines at C-3 has been developed. Mechanistic studies unambiguously support an electrophilic substitution pathway for this transformation.

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Figures

Figure 1
Figure 1
HOMO and LUMO Densities of 1e.
Scheme 1
Scheme 1. Proposed Heck Arylation of Heterocycles
Scheme 2
Scheme 2. Attempts to Perform Heck Reaction on Indolizines
Scheme 3
Scheme 3. Possible Mechanisms for Pd-Catalyzed Arylation of Indolizines
Scheme 4
Scheme 4. Isotope Effect Study
See this image and copyright information in PMC

References

    1. For recent examples, see: Sawada K, Okada S, Kuroda A, Watanabe S, Sawada Y, Tanaka H. Chem Pharm Bull. 2001;49:799.Ostby OB, Dalhus B, Gundersen LL, Rise F, Bast A, Haenen GRMM. Eur J Org Chem. 2000;22:3763.

    1. For recent reviews, see: Michael JP. Alkaloids. 2001;55:91.Michael JP. Nat Prod Rep. 2002;19:742.

    1. See, for example: Halab L, Becker JAJ, Darula Z, Tourwe D, Kieffer BL, Simonin F, Lubell WD. J Med Chem. 2002;45:5353.Pearson WH, Hembre EJ. J Org Chem. 1996;61:5546.

    1. For a review on syntheses and properties of indolizines, see: Behnisch A, Behnisch P, Eggenweiler M, Wallenhorst T Indolizine. Houben-Weyl. 1994;E6b/1, 2a:323–450.

    1. For original papers, see: Chichibabin AE. Chem Ber. 1927;60B:1607.Chichibabin AE, Stepanov FN. Chem Ber. 1929;62B:1068.