Literature DB >> 17576483

Pyridine elaboration through organometallic intermediates: regiochemical control and completeness.

Manfred Schlosser1, Florence Mongin.   

Abstract

Pyridines carrying heterosubstituents (such as carboxy, amido, amino, alkoxy or trifluoromethyl groups or solely individual halogen atoms) can be readily and site selectively metalated. Subsequent reaction with a suitable electrophile opens rational access to a wealth of new building blocks for the synthesis of biologically active compounds. This approach relies on organometallic methods, which are both efficacious and extremely flexible as far as the substitution site and the product structure are concerned (86 references).

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Year:  2007        PMID: 17576483     DOI: 10.1039/b706241a

Source DB:  PubMed          Journal:  Chem Soc Rev        ISSN: 0306-0012            Impact factor:   54.564


  21 in total

1.  Mechanism of Lithium Diisopropylamide-Mediated Ortholithiation of 1,4-Bis(trifluoromethyl)benzene under Nonequilibrium Conditions: Condition-Dependent Rate Limitation and Lithium Chloride-Catalyzed Inhibition.

Authors:  Jun Liang; Alexander C Hoepker; Russell F Algera; Yun Ma; David B Collum
Journal:  J Am Chem Soc       Date:  2015-05-06       Impact factor: 15.419

2.  Computational studies of lithium diisopropylamide deaggregation.

Authors:  Alexander C Hoepker; David B Collum
Journal:  J Org Chem       Date:  2011-09-02       Impact factor: 4.354

3.  Lithium diisopropylamide-mediated ortholithiation of 2-fluoropyridines: rates, mechanisms, and the role of autocatalysis.

Authors:  Lekha Gupta; Alexander C Hoepker; Yun Ma; Mihai S Viciu; Marc F Faggin; David B Collum
Journal:  J Org Chem       Date:  2013-02-08       Impact factor: 4.354

4.  Development of a palladium-catalyzed decarboxylative cross-coupling of (2-azaaryl)carboxylates with aryl halides.

Authors:  Christopher K Haley; Christopher D Gilmore; Brian M Stoltz
Journal:  Tetrahedron       Date:  2013-07-08       Impact factor: 2.457

5.  Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: scope, tunability, and predictability.

Authors:  Fionn O'Hara; Donna G Blackmond; Phil S Baran
Journal:  J Am Chem Soc       Date:  2013-07-30       Impact factor: 15.419

6.  Regioselective lithium diisopropylamide-mediated ortholithiation of 1-chloro-3-(trifluoromethyl)benzene: role of autocatalysis, lithium chloride catalysis, and reversibility.

Authors:  Alexander C Hoepker; Lekha Gupta; Yun Ma; Marc F Faggin; David B Collum
Journal:  J Am Chem Soc       Date:  2011-04-18       Impact factor: 15.419

7.  Synthesis of a 7-azaindole by chichibabin cyclization: reversible base-mediated dimerization of 3-picolines.

Authors:  Yun Ma; Sean Breslin; Ivan Keresztes; Emil Lobkovsky; David B Collum
Journal:  J Org Chem       Date:  2008-12-19       Impact factor: 4.354

8.  Case for Lithium Tetramethylpiperidide-Mediated Ortholithiations: Reactivity and Mechanisms.

Authors:  Kyle A Mack; David B Collum
Journal:  J Am Chem Soc       Date:  2018-03-28       Impact factor: 15.419

Review 9.  Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors:  Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

10.  Lithium diisopropylamide-mediated ortholithiations: lithium chloride catalysis.

Authors:  Lekha Gupta; Alexander C Hoepker; Kanwal J Singh; David B Collum
Journal:  J Org Chem       Date:  2009-03-06       Impact factor: 4.354

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