Literature DB >> 20187653

Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates.

Rui Shang1, Qing Xu, Yuan-Ye Jiang, Yan Wang, Lei Liu.   

Abstract

Pd-catalyzed decarboxylative cross coupling of potassium polyfluorobenzoates with aryl bromides, chlorides, and triflates is achieved by using diglyme as the solvent. The reaction is useful for synthesis of polyfluorobiaryls from readily accessible and nonvolatile polyfluorobenzoate salts. Unlike the Cu-catalyzed decarboxylation cross coupling where oxidative addition is the rate-limiting step, in the Pd-catalyzed version decarboxylation is the rate-limiting step.

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Year:  2010        PMID: 20187653     DOI: 10.1021/ol100008q

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


  8 in total

1.  Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates.

Authors:  Jennifer M Crawford; Kyle E Shelton; Emily K Reeves; Bryce K Sadarananda; Dipannita Kalyani
Journal:  Org Chem Front       Date:  2015-05-12       Impact factor: 5.281

2.  Dual C-F, C-H Functionalization via Photocatalysis: Access to Multifluorinated Biaryls.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  J Am Chem Soc       Date:  2016-02-18       Impact factor: 15.419

3.  Photocatalytic C-F Reduction and Functionalization.

Authors:  Sameera Senaweera; Jimmie D Weaver
Journal:  Aldrichimica Acta       Date:  2016       Impact factor: 3.667

4.  Pd-catalyzed decarboxylative Heck vinylation of 2-nitrobenzoates in the presence of CuF₂.

Authors:  Lukas J Gooßen; Bettina Zimmermann; Thomas Knauber
Journal:  Beilstein J Org Chem       Date:  2010-05-03       Impact factor: 2.883

5.  Nickel-catalyzed decarboxylative cross-coupling of perfluorobenzoates with aryl halides and sulfonates.

Authors:  Logan W Sardzinski; William C Wertjes; Abigail M Schnaith; Dipannita Kalyani
Journal:  Org Lett       Date:  2015-02-20       Impact factor: 6.005

6.  Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings.

Authors:  Gregory J P Perry; Jacob M Quibell; Adyasha Panigrahi; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2017-08-08       Impact factor: 15.419

7.  Benzoate Cyclometalation Enables Oxidative Addition of Haloarenes at a Ru(II) Center.

Authors:  Marco Simonetti; Rositha Kuniyil; Stuart A Macgregor; Igor Larrosa
Journal:  J Am Chem Soc       Date:  2018-09-05       Impact factor: 15.419

8.  A Palladium-Catalyzed 4CzIPN-Mediated Decarboxylative Acylation Reaction of O-Methyl Ketoximes with α-Keto Acids under Visible Light.

Authors:  Cheng Wang; Shan Yang; Zhibin Huang; Yingsheng Zhao
Journal:  Molecules       Date:  2022-03-18       Impact factor: 4.411

  8 in total

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