Literature DB >> 29894188

Catalyzed and Promoted Aliphatic Fluorination.

Desta Doro Bume, Stefan Andrew Harry, Thomas Lectka, Cody Ross Pitts1.   

Abstract

In the last six years, the direct functionalization of aliphatic C-H (and C-C) bonds through user-friendly, radical-based fluorination reactions has emerged as an exciting research area in fluorine chemistry. Considering the historical narratives about the challenges of developing practical radical fluorination in organic frameworks, notable advancements in controlling both reactivity and selectivity have been achieved during this time. As one of the participants in the field, herein, we a provide brief account of research efforts in our laboratory from the initial discovery of radical monofluorination on unactivated C-H bonds in 2012 to more useful strategies to install fluorine on biologically relevant molecules through directed fluorination methods. In addition, accompanying mechanistic studies that have helped guide reaction design are highlighted in context.

Entities:  

Year:  2018        PMID: 29894188     DOI: 10.1021/acs.joc.8b00982

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  7 in total

1.  N-Hydroxybenzimidazole as a structurally modifiable platform for N-oxyl radicals for direct C-H functionalization reactions.

Authors:  Tomomi Yoshii; Saori Tsuzuki; Shunya Sakurai; Ryu Sakamoto; Julong Jiang; Miho Hatanaka; Akira Matsumoto; Keiji Maruoka
Journal:  Chem Sci       Date:  2020-05-18       Impact factor: 9.825

Review 2.  A Survival Guide for the "Electro-curious".

Authors:  Cian Kingston; Maximilian D Palkowitz; Yusuke Takahira; Julien C Vantourout; Byron K Peters; Yu Kawamata; Phil S Baran
Journal:  Acc Chem Res       Date:  2019-12-11       Impact factor: 22.384

3.  N-Directed fluorination of unactivated Csp3-H bonds.

Authors:  Emily N Pinter; Jenna E Bingham; Deyaa I AbuSalim; Silas P Cook
Journal:  Chem Sci       Date:  2019-12-16       Impact factor: 9.825

4.  Csp3-H Trifluoromethylation of Unactivated Aliphatic Systems.

Authors:  Jiachen He; Truong N Nguyen; Shuo Guo; Silas P Cook
Journal:  Org Lett       Date:  2021-01-14       Impact factor: 6.072

5.  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

Review 6.  Oxidative Fluorination of Heteroatoms Enabled by Trichloroisocyanuric Acid and Potassium Fluoride.

Authors:  Yannick Kraemer; Emily Nicole Bergman; Antonio Togni; Cody Ross Pitts
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-21       Impact factor: 16.823

Review 7.  Photosensitized direct C-H fluorination and trifluoromethylation in organic synthesis.

Authors:  Shahboz Yakubov; Joshua P Barham
Journal:  Beilstein J Org Chem       Date:  2020-09-03       Impact factor: 2.883

  7 in total

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