Literature DB >> 27934341

AlkylFluor: Deoxyfluorination of Alcohols.

Nathaniel W Goldberg1, Xiao Shen1, Jiakun Li1,2, Tobias Ritter1,2.   

Abstract

A practical, high-yielding method for the deoxyfluorination of alcohols is presented using AlkylFluor, a novel salt analogue of PhenoFluor. AlkylFluor is readily prepared on multigram scale and is stable to long-term storage in air and exposure to water. The practicality and applicability of this method is demonstrated with a variety of primary and secondary alcohol substrates.

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Year:  2016        PMID： 27934341      PMCID： PMC5582538          DOI： 10.1021/acs.orglett.6b03086

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


  11 in total

1.  Introduction of fluorine and fluorine-containing functional groups.

Authors:  Theresa Liang; Constanze N Neumann; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2013-07-19       Impact factor: 15.336

2.  Late-stage fluorination: fancy novelty or useful tool?

Authors:  Constanze N Neumann; Tobias Ritter
Journal:  Angew Chem Int Ed Engl       Date:  2015-02-04       Impact factor: 15.336

3.  PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.

Authors:  Matthew K Nielsen; Christian R Ugaz; Wenping Li; Abigail G Doyle
Journal:  J Am Chem Soc       Date:  2015-07-21       Impact factor: 15.419

4.  Deoxyfluorination of phenols.

Authors:  Pingping Tang; Weike Wang; Tobias Ritter
Journal:  J Am Chem Soc       Date:  2011-07-12       Impact factor: 15.419

5.  Good partnership between sulfur and fluorine: sulfur-based fluorination and fluoroalkylation reagents for organic synthesis.

Authors:  Chuanfa Ni; Mingyou Hu; Jinbo Hu
Journal:  Chem Rev       Date:  2014-08-21       Impact factor: 60.622

6.  Discovery of 4-tert-butyl-2,6-dimethylphenylsulfur trifluoride as a deoxofluorinating agent with high thermal stability as well as unusual resistance to aqueous hydrolysis, and its diverse fluorination capabilities including deoxofluoro-arylsulfinylation with high stereoselectivity.

Authors:  Teruo Umemoto; Rajendra P Singh; Yong Xu; Norimichi Saito
Journal:  J Am Chem Soc       Date:  2010-12-02       Impact factor: 15.419

Review 7.  Transition metal catalysis and nucleophilic fluorination.

Authors:  Charlotte Hollingworth; Véronique Gouverneur
Journal:  Chem Commun (Camb)       Date:  2012-02-15       Impact factor: 6.222

8.  PhenoFluorMix: practical chemoselective deoxyfluorination of phenols.

Authors:  Teppei Fujimoto; Tobias Ritter
Journal:  Org Lett       Date:  2015-01-26       Impact factor: 6.005

9.  Aminodifluorosulfinium tetrafluoroborate salts as stable and crystalline deoxofluorinating reagents.

Authors:  Francis Beaulieu; Louis-Philippe Beauregard; Gabriel Courchesne; Michel Couturier; François LaFlamme; Alexandre L'Heureux
Journal:  Org Lett       Date:  2009-11-05       Impact factor: 6.005

10.  PhenoFluor: Practical Synthesis, New Formulation, and Deoxyfluorination of Heteroaromatics.

Authors:  Teppei Fujimoto; Fabian Becker; Tobias Ritter
Journal:  Org Process Res Dev       Date:  2014-07-23       Impact factor: 3.317
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  8 in total

1.  Fluorinated Amine Stereotriads via Allene Amination.

Authors:  Lu Liu; Nels C Gerstner; Lucas J Oxtoby; Ilia A Guzei; Jennifer M Schomaker
Journal:  Org Lett       Date:  2017-06-02       Impact factor: 6.005

2.  Light-Mediated Formal Radical Deoxyfluorination of Tertiary Alcohols through Selective Single-Electron Oxidation with TEDA2+.

Authors:  Francisco José Aguilar Troyano; Frederic Ballaschk; Marcel Jaschinski; Yasemin Özkaya; Adrián Gómez-Suárez
Journal:  Chemistry       Date:  2019-10-18       Impact factor: 5.236

3.  A Pd-Catalyzed [4 + 2] Annulation Approach to Fluorinated N-Heterocycles.

Authors:  Víctor García-Vázquez; Larry Hoteite; Christopher P Lakeland; David W Watson; Joseph P A Harrity
Journal:  Org Lett       Date:  2021-03-24       Impact factor: 6.005

4.  Renewable Reagent for Nucleophilic Fluorination.

Authors:  Blaž Alič; Jan Petrovčič; Jan Jelen; Gašper Tavčar; Jernej Iskra
Journal:  J Org Chem       Date:  2022-04-19       Impact factor: 4.198

5.  The formation of all-cis-(multi)fluorinated piperidines by a dearomatization-hydrogenation process.

Authors:  Zackaria Nairoukh; Marco Wollenburg; Christoph Schlepphorst; Klaus Bergander; Frank Glorius
Journal:  Nat Chem       Date:  2019-01-21       Impact factor: 24.427

6.  Enantiospecific deoxyfluorination of cyclic α-OH-β-ketoesters.

Authors:  Christopher Mairhofer; Victoria Haider; Thomas Bögl; Mario Waser
Journal:  Org Biomol Chem       Date:  2021-01-06       Impact factor: 3.876

7.  Catalytic Enantioselective Synthesis of Heterocyclic Vicinal Fluoroamines by Using Asymmetric Protonation: Method Development and Mechanistic Study.

Authors:  Matthew W Ashford; Chao Xu; John J Molloy; Cameron Carpenter-Warren; Alexandra M Z Slawin; Andrew G Leach; Allan J B Watson
Journal:  Chemistry       Date:  2020-08-18       Impact factor: 5.236

Review 8.  Closing the gap between 19F and 18F chemistry.

Authors:  Javier Ajenjo; Gianluca Destro; Bart Cornelissen; Véronique Gouverneur
Journal:  EJNMMI Radiopharm Chem       Date:  2021-09-25
  8 in total

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