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Literature DB >> 18681436

Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts.

Alexey B Zaitsev¹, Stefan Gruber, Pascal A Plüss, Paul S Pregosin, Luis F Veiros, Michael Wörle.

Abstract

New Ru-sulfonate catalysts have been synthesized and shown to very rapidly allylate indole and pyrrole compounds using allyl alcohols as substrates. The observed regioselectivity is exceptionally high (up to 100% of the branched isomer). Density functional theory calculations explain these results.

Entities: Chemical

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Year: 2008 PMID： 18681436 DOI： 10.1021/ja804379k

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

8 in total

1. Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

Authors: Seung Wook Kim; Tabitha T Schempp; Jason R Zbieg; Craig E Stivala; Michael J Krische
Journal: Angew Chem Int Ed Engl Date: 2019-05-06 Impact factor: 15.336

2. Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

Authors: Takashi Nishikata; Bruce H Lipshutz
Journal: J Am Chem Soc Date: 2009-09-02 Impact factor: 15.419

3. Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.

Authors: Ruili Gao; Chae S Yi
Journal: J Org Chem Date: 2010-05-07 Impact factor: 4.354

Fast and highly regioselective allylation of indole and pyrrole compounds by allyl alcohols using Ru-sulfonate catalysts.

1. Regio- and Enantioselective Iridium-Catalyzed N-Allylation of Indoles and Related Azoles with Racemic Branched Alkyl-Substituted Allylic Acetates.

2. Allylic ethers as educts for Suzuki-Miyaura couplings in water at room temperature.

3. Regioselective formation of alpha-vinylpyrroles from the ruthenium-catalyzed coupling reaction of pyrroles and terminal alkynes involving C-H bond activation.

4. Alkyne Hydroheteroarylation: Enantioselective Coupling of Indoles and Alkynes via Rh-Hydride Catalysis.

5. A review of new developments in the Friedel-Crafts alkylation - From green chemistry to asymmetric catalysis.

6. Asymmetric synthesis of N-allylic indoles via regio- and enantioselective allylation of aryl hydrazines.

7. Platinum-Catalyzed Allylation of 2,3-Disubstituted Indoles with Allylic Acetates.

8. Aqua-bis-(4-methyl-benzene-sulfonato-κO)(η(5)-penta-methyl-cyclo-penta-dien-yl)rhodium(III) monohydrate.