Literature DB >> 33767531

Electrochemical C(sp3)-H Fluorination.

Yusuke Takahira1, Miao Chen1, Yu Kawamata1, Pavel Mykhailiuk1,2, Hugh Nakamura1, Byron K Peters1, Solomon H Reisberg1, Chao Li1, Longrui Chen3, Tamaki Hoshikawa4, Tomoyuki Shibuguchi4, Phil S Baran1.   

Abstract

A simple and robust method for electrochemical alkyl C-H fluorination is presented. Using a simple nitrate additive, a widely available fluorine source (Selectfluor), and carbon-based electrodes, a wide variety of activated and unactivated C-H bonds were converted to their C-F congeners. The scalability of the reaction was also demonstrated with a 100 gram preparation of fluorovaline.

Entities:  

Keywords:  C–H functionalization; electrochemistry; fluorination; organic synthesis; radical

Year:  2019        PMID: 33767531      PMCID: PMC7990259          DOI: 10.1055/s-0037-1611737

Source DB:  PubMed          Journal:  Synlett        ISSN: 0936-5214            Impact factor:   2.454


  7 in total

1.  Bismuth-catalyzed arylation of ethyl glyoxylate with aniline via N-H insertion.

Authors:  Mohd Aamir Bin Riyaz; G Premkumar; Toka Swu
Journal:  Mol Divers       Date:  2022-03-17       Impact factor: 2.943

2.  Hydroxy-directed fluorination of remote unactivated C(sp3)-H bonds: a new age of diastereoselective radical fluorination.

Authors:  Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal:  Chem Sci       Date:  2022-05-30       Impact factor: 9.969

Review 3.  Reproducibility in Electroorganic Synthesis-Myths and Misunderstandings.

Authors:  Sebastian B Beil; Dennis Pollok; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2021-03-03       Impact factor: 15.336

4.  A Practical and Scalable Approach to Fluoro-Substituted Bicyclo[1.1.1]pentanes.

Authors:  Roman Bychek; Pavel K Mykhailiuk
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-14       Impact factor: 16.823

5.  Metal-free electrochemical fluorodecarboxylation of aryloxyacetic acids to fluoromethyl aryl ethers.

Authors:  Michael Berger; John D Herszman; Yuji Kurimoto; Goswinus H M de Kruijff; Aaron Schüll; Sven Ruf; Siegfried R Waldvogel
Journal:  Chem Sci       Date:  2020-06-01       Impact factor: 9.825

Review 6.  Synthetic Molecular Photoelectrochemistry: New Frontiers in Synthetic Applications, Mechanistic Insights and Scalability.

Authors:  Shangze Wu; Jaspreet Kaur; Tobias A Karl; Xianhai Tian; Joshua P Barham
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-09       Impact factor: 16.823

Review 7.  Bridge Functionalisation of Bicyclo[1.1.1]pentane Derivatives.

Authors:  Joseph M Anderson; Nicholas D Measom; John A Murphy; Darren L Poole
Journal:  Angew Chem Int Ed Engl       Date:  2021-08-07       Impact factor: 16.823

  7 in total

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