Literature DB >> 25045137

Mild and versatile nitrate-promoted C-H bond fluorination.

Shao-Jie Lou1, Dan-Qian Xu, Zhen-Yuan Xu.   

Abstract

A novel and facile C-H bond fluorination proceeds under remarkably mild conditions (close to room temperature in most cases). Both aromatic and olefinic C(sp(2))-H bonds with a wide range of electronic properties are selectively fluorinated in the presence of a catalytic amount of simple, cheap, and nontoxic nitrate as the promoter. A Pd(II)/Pd(IV) catalytic cycle that is initiated by an in situ generated cationic [Pd(NO3)](+) species was proposed based on preliminary mechanistic studies.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CH activation; alkenes; fluorination; nitrate; room temperature

Mesh:

Substances:

Year:  2014        PMID: 25045137     DOI: 10.1002/anie.201404423

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  6 in total

1.  Copper-Mediated Fluorination of Aryl Trisiloxanes with Nucleophilic Fluoride.

Authors:  Ruth Dorel; Philip Boehm; Daniel P Schwinger; John F Hartwig
Journal:  Chemistry       Date:  2020-01-28       Impact factor: 5.236

2.  Ligand-Enabled Stereoselective β-C(sp(3))-H Fluorination: Synthesis of Unnatural Enantiopure anti-β-Fluoro-α-amino Acids.

Authors:  Ru-Yi Zhu; Keita Tanaka; Gen-Cheng Li; Jian He; Hai-Yan Fu; Su-Hua Li; Jin-Quan Yu
Journal:  J Am Chem Soc       Date:  2015-05-27       Impact factor: 15.419

3.  Synthesis of Cyclic Anhydrides via Ligand-Enabled C-H Carbonylation of Simple Aliphatic Acids.

Authors:  Zhe Zhuang; Alastair N Herron; Jin-Quan Yu
Journal:  Angew Chem Int Ed Engl       Date:  2021-06-17       Impact factor: 16.823

Review 4.  Recent advances in transition-metal-catalyzed incorporation of fluorine-containing groups.

Authors:  Xiaowei Li; Xiaolin Shi; Xiangqian Li; Dayong Shi
Journal:  Beilstein J Org Chem       Date:  2019-09-23       Impact factor: 2.883

5.  Relative Strength of Common Directing Groups in Palladium-Catalyzed Aromatic C-H Activation.

Authors:  Anna Tomberg; Michael Éric Muratore; Magnus Jan Johansson; Ina Terstiege; Christian Sköld; Per-Ola Norrby
Journal:  iScience       Date:  2019-09-27

6.  Pd(ii)-catalyzed remote regiodivergent ortho- and meta-C-H functionalizations of phenylethylamines.

Authors:  Shangda Li; Huafang Ji; Lei Cai; Gang Li
Journal:  Chem Sci       Date:  2015-06-25       Impact factor: 9.825

  6 in total

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