Literature DB >> 14575491

Scope of Ru(II)-catalyzed synthesis of pyridines from alkynes and nitriles.

Jesús A Varela1, Luis Castedo, Carlos Saá.   

Abstract

Pyridines can be efficiently synthesized by Ru(II)-catalyzed [2 + 2 + 2] cycloaddition of 1,6-diynes to alpha,omega-dinitriles or electron-deficient nitriles or by Ru(II)-catalyzed [2 + 2 + 2] cocyclization of electron-deficient alkynes and electron-deficient nitriles. The reactions with dinitriles seem likely to proceed via ruthenacyclopentadiene intermediates and the reactions with electron-poor nitriles via azaruthenacyclopentadienes. The reaction with asymmetric electron-deficient alkynes affords 2,3,6-trisubstituted pyridines in good yield.

Entities:  

Year:  2003        PMID： 14575491     DOI： 10.1021/jo035050b

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


  9 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.  Why nature eschews the concerted [2 + 2 + 2] cycloaddition of a nonconjugated cyanodiyne. Computational study of a pyridine synthesis involving an ene-Diels-Alder-bimolecular hydrogen-transfer mechanism.

Authors:  Yu Lan; Rick L Danheiser; K N Houk
Journal:  J Org Chem       Date:  2012-01-25       Impact factor: 4.354

4.  Iron-catalyzed cycloaddition of alkynenitriles and alkynes.

Authors:  Brendan R D'Souza; Timothy K Lane; Janis Louie
Journal:  Org Lett       Date:  2011-05-10       Impact factor: 6.005

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.  Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: synthesis of 4-haloisoxazoles and 5-halotriazoles.

Authors:  James S Oakdale; Rakesh K Sit; Valery V Fokin
Journal:  Chemistry       Date:  2014-07-24       Impact factor: 5.236

7.  Mechanistic Evaluation of the Ni(IPr)2-Catalyzed Cycloaddition of Alkynes and Nitriles to Afford Pyridines: Evidence for the Formation of a Key η1-Ni(IPr)2(RCN) Intermediate.

Authors:  Ryan M Stolley; Hung A Duong; Janis Louie
Journal:  Organometallics       Date:  2013-09-09       Impact factor: 3.876

Review 8.  Ruthenium-Catalyzed Cycloadditions to Form Five-, Six-, and Seven-Membered Rings.

Authors:  Rosalie S Doerksen; Tomáš Hodík; Guanyu Hu; Nancy O Huynh; William G Shuler; Michael J Krische
Journal:  Chem Rev       Date:  2021-02-12       Impact factor: 60.622

9.  Practical Synthesis of α-Trifluoromethylated Pyridines Based on Regioselective Cobalt-Catalyzed [2+2+2] Cycloaddition using Trifluoromethylated Diynes with Nitriles.

Authors:  Tatsuya Kumon; Shigeyuki Yamada; Tomohiro Agou; Hiroki Fukumoto; Toshio Kubota; Gerald B Hammond; Tsutomu Konno
Journal:  Adv Synth Catal       Date:  2021-01-22       Impact factor: 5.837
  9 in total

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