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Literature DB >> 15366880

Nickel-catalyzed cycloaddition of alkynes and isocyanates.

Hung A Duong¹, Michael J Cross, Janis Louie.

Abstract

A mild and general route for preparing 2-pyridones from isocyanates and diynes is described. Ni imidazolyidene complexes were used to mediate cyclizations between both internal and terminal diynes with aryl and alkyl isocyanates. In addition, the efficacy of this protocol allows for the preparation of a fused seven-membered pyridone and for three component cyclizations.

Entities: Chemical

Year: 2004 PMID： 15366880 DOI： 10.1021/ja046477i

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

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Cited

23 in total

1. Asymmetric synthesis of bicyclic amidines via rhodium-catalyzed [2+2+2] cycloaddition of carbodiimides.

Authors: Robert T Yu; Tomislav Rovis
Journal: J Am Chem Soc Date: 2008-02-27 Impact factor: 15.419

2. Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

Authors: Rebecca Keller Friedman; Kevin M Oberg; Derek M Dalton; Tomislav Rovis
Journal: Pure Appl Chem Date: 2009-07-01 Impact factor: 2.453

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. Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.

Authors: Ryan M Stolley; Michael T Maczka; Janis Louie
Journal: European J Org Chem Date: 2011-07

5. Nickel-Catalyzed Cycloisomerization of Enynes: Catalyst Generation via C-H Activation of Carbene Ligands.

Authors: Thomas N Tekavec; Janis Louie
Journal: Tetrahedron Date: 2008-07-14 Impact factor: 2.457

6. Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

Authors: Ernest E Lee; Tomislav Rovis
Journal: Org Lett Date: 2008-02-20 Impact factor: 6.005

Nickel-catalyzed cycloaddition of alkynes and isocyanates.

1. Asymmetric synthesis of bicyclic amidines via rhodium-catalyzed [2+2+2] cycloaddition of carbodiimides.

2. Phosphoramidite-Rhodium Complexes as Catalysts for the Asymmetric [2+2+2] Cycloaddition of Alkenyl Isocyanates and Alkynes.

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

4. Nickel-Catalyzed [2+2+2] Cycloaddition of Diynes and Cyanamides.

5. Nickel-Catalyzed Cycloisomerization of Enynes: Catalyst Generation via C-H Activation of Carbene Ligands.

6. Enantioselective synthesis of indolizidines bearing quaternary substituted stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of alkenyl isocyanates and terminal alkynes.

7. Nickel-catalyzed cycloaddition of 1,3-dienes with 3-azetidinones and 3-oxetanones.

8. Nickel-catalyzed reactions of vinyl aziridines and aziridinylen-ynes.

9. The discovery of [Ni(NHC)RCN]2 species and their role as cycloaddition catalysts for the formation of pyridines.

10. The iron-catalyzed construction of 2-aminopyrimidines from alkynenitriles and cyanamides.