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Literature DB >> 19772313

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.

Aaron Aponick¹, Chuan-Ying Li, Jeremy Malinge, Emerson Finco Marques.

Abstract

Furans, pyrroles, and thiophenes are efficiently prepared by gold-catalyzed dehydrative cyclizations of readily available, heteroatom-substituted propargylic alcohols. The reactions are rapid, high-yielding, and procedurally simple, giving essentially pure aromatic heterocycles in minutes under open-flask conditions with catalyst loadings as low as 0.05 mol %.

Entities: Chemical

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Year: 2009 PMID： 19772313 DOI： 10.1021/ol901901m

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

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Cited

22 in total

1. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

Authors: Alexander S Dudnik; Yuanzhi Xia; Yahong Li; Vladimir Gevorgyan
Journal: J Am Chem Soc Date: 2010-06-09 Impact factor: 15.419

2. Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis.

Authors: Yong Li; Mingji Dai
Journal: Angew Chem Int Ed Engl Date: 2017-08-10 Impact factor: 15.336

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

Authors: Anton V Gulevich; Alexander S Dudnik; Natalia Chernyak; Vladimir Gevorgyan
Journal: Chem Rev Date: 2013-01-10 Impact factor: 60.622

4. One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.

Authors: Liliya V Frolova; Nikolai M Evdokimov; Kathryn Hayden; Indranil Malik; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal: Org Lett Date: 2011-01-26 Impact factor: 6.005

An extremely facile synthesis of furans, pyrroles, and thiophenes by the dehydrative cyclization of propargyl alcohols.

1. Computation-guided development of Au-catalyzed cycloisomerizations proceeding via 1,2-Si or 1,2-H migrations: regiodivergent synthesis of silylfurans.

2. Total Syntheses of the Reported Structures of Curcusones I and J through Tandem Gold Catalysis.

Review 3. Transition metal-mediated synthesis of monocyclic aromatic heterocycles.

4. One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.

5. Gold(I)-catalyzed amination of allylic alcohols with cyclic ureas and related nucleophiles.

6. Pyrrole-based scaffolds for turn mimics.

7. Gold(I)-catalyzed intramolecular amination of allylic alcohols with alkylamines.

8. Leveraging the micellar effect: gold-catalyzed dehydrative cyclizations in water at room temperature.

9. Gold Catalysis-Facilitated Rapid Synthesis of the Daphnane/Tigliane Tricyclic Core.

10. Gold(I)-catalyzed formation of furans by a Claisen-type rearrangement of ynenyl allyl ethers.