Literature DB >> 16839179

An in situ approach for nickel-catalyzed cycloaddition.

Thomas N Tekavec1, Gang Zuo, Kristina Simon, Janis Louie.   

Abstract

A convenient method for preparing pyridines from air-stable, commercially available catalyst precursors is described. The addition of n-BuLi to Ni(acac)2 and an NHC salt (such as IPr.HCl or SIPr.HCl) rapidly generates an active Ni0/NHC catalyst for the cycloaddition of diynes and nitriles that affords pyridines without a decrease in observed yields. The in situ method also converts diynes and carbon dioxide to the corresponding pyrones.

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Year:  2006        PMID: 16839179     DOI: 10.1021/jo0608669

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  6 in total

1.  A serendipitous discovery: nickel catalyst for the cycloaddition of diynes with unactivated nitriles.

Authors:  Puneet Kumar; Simon Prescher; Janis Louie
Journal:  Angew Chem Int Ed Engl       Date:  2011-09-20       Impact factor: 15.336

Review 2.  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

3.  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

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

Authors:  Gang Zuo; Kainan Zhang; Janis Louie
Journal:  Tetrahedron Lett       Date:  2008-11-24       Impact factor: 2.415

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

Authors:  Ryan M Stolley; Hung A Duong; David R Thomas; Janis Louie
Journal:  J Am Chem Soc       Date:  2012-09-04       Impact factor: 15.419

6.  Nickel-catalyzed cycloadditive couplings of enynes and isocyanates.

Authors:  Brendan R D'Souza; Janis Louie
Journal:  Org Lett       Date:  2009-09-17       Impact factor: 6.005

  6 in total

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