Literature DB >> 25866198

Iron- or silver-catalyzed oxidative fluorination of cyclopropanols for the synthesis of β-fluoroketones.

Shichao Ren1, Chao Feng, Teck-Peng Loh.   

Abstract

The Fe(III)- or Ag(I)-catalyzed oxidative fluorination of cyclopropanols via radical rearrangement is disclosed. This process features a straightforward and highly effective protocol for the site-specific synthesis of β-fluoroketones and represents an expedient method for the synthesis of γ-, δ- and ε-fluoroketones. Notably, this reaction proceeds at room temperature and tolerates a diverse array of cyclopropanols.

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Year:  2015        PMID: 25866198     DOI: 10.1039/c5ob00632e

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN: 1477-0520            Impact factor:   3.876


  7 in total

1.  Deconstructive fluorination of cyclic amines by carbon-carbon cleavage.

Authors:  Jose B Roque; Yusuke Kuroda; Lucas T Göttemann; Richmond Sarpong
Journal:  Science       Date:  2018-07-13       Impact factor: 47.728

2.  Direct Access to β-Fluorinated Aldehydes by Nitrite-Modified Wacker Oxidation.

Authors:  Crystal K Chu; Daniel T Ziegler; Brian Carr; Zachary K Wickens; Robert H Grubbs
Journal:  Angew Chem Int Ed Engl       Date:  2016-05-25       Impact factor: 15.336

3.  Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds.

Authors:  Hatice G Yayla; Huaiju Wang; Kyle T Tarantino; Hudson S Orbe; Robert R Knowles
Journal:  J Am Chem Soc       Date:  2016-08-18       Impact factor: 15.419

4.  Unstrained C-C bond activation and directed fluorination through photocatalytically-generated radical cations.

Authors:  Cody Ross Pitts; Michelle Sheanne Bloom; Desta Doro Bume; Qinze Arthur Zhang; Thomas Lectka
Journal:  Chem Sci       Date:  2015-06-23       Impact factor: 9.825

Review 5.  Catalytic generation of alkoxy radicals from unfunctionalized alcohols.

Authors:  Elaine Tsui; Huaiju Wang; Robert R Knowles
Journal:  Chem Sci       Date:  2020-09-21       Impact factor: 9.825

6.  Divergent reactivities in fluoronation of allylic alcohols: synthesis of Z-fluoroalkenes via carbon-carbon bond cleavage.

Authors:  Tang-Lin Liu; Ji'En Wu; Yu Zhao
Journal:  Chem Sci       Date:  2017-03-20       Impact factor: 9.825

7.  Visible light-promoted ring-opening functionalization of unstrained cycloalkanols via inert C-C bond scission.

Authors:  Dongping Wang; Jincheng Mao; Chen Zhu
Journal:  Chem Sci       Date:  2018-06-11       Impact factor: 9.825

  7 in total

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