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Literature DB >> 18800797

Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes.

José Barluenga¹, Lorena Riesgo, Rubén Vicente, Luis A López, Miguel Tomás.

Abstract

Polysubstituted furan derivatives are regioselective obtained from (bis-alkynyl)methyl carboxylates in the presence of catalytic amounts of copper(I) salts. This multistep process is consistent with the intermediacy of a copper(I) (2-furyl)carbene complex which is intercepted by suitable trapping reagents.

Entities: Chemical

Year: 2008 PMID： 18800797 DOI： 10.1021/ja8058342

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

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Cited

9 in total

Review 1. Aerobic copper-catalyzed organic reactions.

Authors: Scott E Allen; Ryan R Walvoord; Rosaura Padilla-Salinas; Marisa C Kozlowski
Journal: Chem Rev Date: 2013-06-20 Impact factor: 60.622

2. 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

Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes.

Review 1. Aerobic copper-catalyzed organic reactions.

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

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

4. An expedient route to substituted furans via olefin cross-metathesis.

5. Incorporation of hexafluorobutyne into furans or phenols via reaction with iron(0) carbene or vinylketene complexes.

6. Multicomponent type II anion relay chemistry (ARC): one-pot syntheses of 2,3-disubstituted furans and thiophenes.

7. Multicomponent formation route to a new class of oxygen-based 1,3-dipoles and the modular synthesis of furans.

8. Gold(iii) promoted formation of dihydroquinazolinones: double X-H activation by gold.

9. Photocatalytic synthesis of tetra-substituted furans promoted by carbon dioxide.