Literature DB >> 24156393

Synthesis of solid 2-pyridylzinc reagents and their application in Negishi reactions.

James R Colombe1, Sebastian Bernhardt, Christos Stathakis, Stephen L Buchwald, Paul Knochel.   

Abstract

In search of alternatives to unstable or unreliable 2-pyridylboron reagents, we have explored two new varieties of solid, moderately air-stable 2-pyridylzinc reagents. Both reagents can be manipulated in air and are competent nucleophiles in Negishi cross-coupling reactions.

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Year:  2013        PMID： 24156393      PMCID： PMC3869385          DOI： 10.1021/ol402798z

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  22 in total

1.  Microwave-assisted Negishi and Kumada cross-coupling reactions of aryl chlorides.

Authors:  Peter Walla; C Oliver Kappe
Journal:  Chem Commun (Camb)       Date:  2004-01-30       Impact factor: 6.222

Review 2.  Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors:  Christopher K Prier; Danica A Rankic; David W C MacMillan
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3.  A new palladium precatalyst allows for the fast Suzuki-Miyaura coupling reactions of unstable polyfluorophenyl and 2-heteroaryl boronic acids.

Authors:  Tom Kinzel; Yong Zhang; Stephen L Buchwald
Journal:  J Am Chem Soc       Date:  2010-10-13       Impact factor: 15.419

4.  Palladium-catalyzed Suzuki-Miyaura coupling of pyridyl-2-boronic esters with aryl halides using highly active and air-stable phosphine chloride and oxide ligands.

Authors:  David X Yang; Steven L Colletti; Kevin Wu; Maoying Song; George Y Li; Hong C Shen
Journal:  Org Lett       Date:  2009-01-15       Impact factor: 6.005

5.  Aerobic oxidative Heck/dehydrogenation reactions of cyclohexenones: efficient access to meta-substituted phenols.

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6.  Scope of the Suzuki-Miyaura cross-coupling reactions of potassium heteroaryltrifluoroborates.

Authors:  Gary A Molander; Belgin Canturk; Lauren E Kennedy
Journal:  J Org Chem       Date:  2009-02-06       Impact factor: 4.354

7.  TMPZnOPiv•LiCl: a new base for the preparation of air-stable solid zinc pivalates of sensitive aromatics and heteroaromatics.

Authors:  Christos I Stathakis; Sophia M Manolikakes; Paul Knochel
Journal:  Org Lett       Date:  2013-03-05       Impact factor: 6.005

8.  Cyclic triolborates: air- and water-stable ate complexes of organoboronic acids.

Authors:  Yasunori Yamamoto; Miho Takizawa; Xiao-Qiang Yu; Norio Miyaura
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

9.  A general solution for the 2-pyridyl problem.

Authors:  Graham R Dick; Eric M Woerly; Martin D Burke
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-27       Impact factor: 15.336
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  12 in total

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Authors:  Marcus E Farmer; Phil S Baran
Journal:  Nature       Date:  2015-08-13       Impact factor: 49.962

2.  Exhaustive Suzuki-Miyaura reactions of polyhalogenated heteroarenes with alkyl boronic pinacol esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Chem Commun (Camb)       Date:  2017-06-29       Impact factor: 6.222

3.  Nonsymmetrical Bis-Azine Biaryls from Chloroazines: A Strategy Using Phosphorus Ligand-Coupling.

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Journal:  J Am Chem Soc       Date:  2019-09-16       Impact factor: 15.419

4.  Well-defined nickel and palladium precatalysts for cross-coupling.

Authors:  Nilay Hazari; Patrick R Melvin; Megan Mohadjer Beromi
Journal:  Nat Rev Chem       Date:  2017-03-01       Impact factor: 34.035

5.  Synthesis of Heteroaryl Sulfonamides from Organozinc Reagents and 2,4,6-Trichlorophenyl Chlorosulfate.

Authors:  James R Colombe; J Robb DeBergh; Stephen L Buchwald
Journal:  Org Lett       Date:  2015-06-11       Impact factor: 6.005

6.  Selective and Serial Suzuki-Miyaura Reactions of Polychlorinated Aromatics with Alkyl Pinacol Boronic Esters.

Authors:  Sébastien Laulhé; J Miles Blackburn; Jennifer L Roizen
Journal:  Org Lett       Date:  2016-08-18       Impact factor: 6.005

7.  Organozinc pivalates for cobalt-catalyzed difluoroalkylarylation of alkenes.

Authors:  Xinyi Cheng; Xingchen Liu; Shengchun Wang; Ying Hu; Binjing Hu; Aiwen Lei; Jie Li
Journal:  Nat Commun       Date:  2021-07-16       Impact factor: 14.919

8.  Dosage delivery of sensitive reagents enables glove-box-free synthesis.

Authors:  Aaron C Sather; Hong Geun Lee; James R Colombe; Anni Zhang; Stephen L Buchwald
Journal:  Nature       Date:  2015-08-13       Impact factor: 49.962

9.  Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines.

Authors:  Dimitra Kontokosta; Daniel S Mueller; Dong-Liang Mo; Wiktoria H Pace; Rachel A Simpson; Laura L Anderson
Journal:  Beilstein J Org Chem       Date:  2015-11-04       Impact factor: 2.883

10.  Cobalt-catalyzed acylation-reactions of (hetero)arylzinc pivalates with thiopyridyl ester derivatives.

Authors:  Ferdinand H Lutter; Lucie Grokenberger; Maximilian S Hofmayer; Paul Knochel
Journal:  Chem Sci       Date:  2019-07-11       Impact factor: 9.825
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