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Literature DB >> 12556177

Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene.

Bobby Glover¹, Kimberly A Harvey, Bing Liu, Matthew J Sharp, Maria F Tymoschenko.

Abstract

[reaction: see text] The regioselective palladium(0)-catalyzed arylation of 3-furoate and 3-thiophenecarboxylate esters with aryl bromides is described. Conditions were developed that allow for the selective synthesis of either 2-aryl or 5-aryl products.

Entities: Chemical

Mesh：

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Year: 2003 PMID： 12556177 DOI： 10.1021/ol027266q

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

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Cited

15 in total

Review 1. Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

Authors: Ilya V Seregin; Vladimir Gevorgyan
Journal: Chem Soc Rev Date: 2007-03-05 Impact factor: 54.564

2. Direct palladium-catalyzed alkynylation of N-fused heterocycles.

Authors: Ilya V Seregin; Victoria Ryabova; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2007-06-01 Impact factor: 15.419

3. Direct Pd-catalyzed arylation of 1,2,3-triazoles.

Authors: Stepan Chuprakov; Natalia Chernyak; Alexander S Dudnik; Vladimir Gevorgyan
Journal: Org Lett Date: 2007-05-10 Impact factor: 6.005

4. Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by "ligandless" species.

Authors: Yichen Tan; John F Hartwig
Journal: J Am Chem Soc Date: 2011-02-11 Impact factor: 15.419

5. Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

Authors: Caleb Karmel; Camille Z Rubel; Elena V Kharitonova; John F Hartwig
Journal: Angew Chem Weinheim Bergstr Ger Date: 2020-01-22

6. Bis-N-heterocyclic carbene palladium(IV) tetrachloride complexes: synthesis, reactivity, and mechanisms of direct chlorinations and oxidations of organic substrates.

Authors: A Scott McCall; Hongwang Wang; John M Desper; Stefan Kraft
Journal: J Am Chem Soc Date: 2011-01-19 Impact factor: 15.419

Regioselective palladium-catalyzed arylation of 3-carboalkoxy furan and thiophene.

Review 1. Direct transition metal-catalyzed functionalization of heteroaromatic compounds.

2. Direct palladium-catalyzed alkynylation of N-fused heterocycles.

3. Direct Pd-catalyzed arylation of 1,2,3-triazoles.

4. Assessment of the intermediacy of arylpalladium carboxylate complexes in the direct arylation of benzene: evidence for C-H bond cleavage by "ligandless" species.

5. Iridium-Catalyzed Silylation of Five-Membered Heteroarenes: High Sterically Derived Selectivity from a Pyridyl-Imidazoline Ligand.

6. Bis-N-heterocyclic carbene palladium(IV) tetrachloride complexes: synthesis, reactivity, and mechanisms of direct chlorinations and oxidations of organic substrates.

7. Investigating the dearomative rearrangement of biaryl phosphine-ligated Pd(II) complexes.

8. Palladium-catalyzed arylation and heteroarylation of indolizines.

9. Rh(I)-catalyzed arylation of heterocycles via C-H bond activation: expanded scope through mechanistic insight.

10. Direct Arylation of Benzo[b]furan and Other Benzo-Fused Heterocycles.