Literature DB >> 30557030

Electrochemical Fluorocyclization of N-Allylcarboxamides to 2-Oxazolines by Hypervalent Iodine Mediator.

John D Haupt1, Michael Berger1, Siegfried R Waldvogel1.   

Abstract

A resource saving protocol for the synthesis of 5-fluoromethyl-2-oxazolines by using electrochemistry has been realized. Thereby, a hypervalent iodine species I(III) is generated by anodic oxidation in the presence of Et3N·5HF and mediates the cyclization of N-allylcarboxamide to 5-fluoromethyl-2-oxazoline. This method allows application to various substrates furnishing the 2-oxazolines with yields up to 68%. The protocol is easy to conduct under constant current conditions offering a sustainable alternative over conventional reagent-based pathways.

Entities:  

Year:  2018        PMID： 30557030     DOI： 10.1021/acs.orglett.8b03682

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


  11 in total

Review 1.  Recent Updates on Electrogenerated Hypervalent Iodine Derivatives and Their Applications as Mediators in Organic Electrosynthesis.

Authors:  Chaoyue Chen; Xin Wang; Tinghai Yang
Journal:  Front Chem       Date:  2022-04-13       Impact factor: 5.545

2.  C-H Oxygenation Reactions Enabled by Dual Catalysis with Electrogenerated Hypervalent Iodine Species and Ruthenium Complexes.

Authors:  Leonardo Massignan; Xuefeng Tan; Tjark H Meyer; Rositha Kuniyil; Antonis M Messinis; Lutz Ackermann
Journal:  Angew Chem Int Ed Engl       Date:  2020-01-09       Impact factor: 15.336

3.  A mild catalytic synthesis of 2-oxazolines via oxetane ring-opening: rapid access to a diverse family of natural products.

Authors:  Hai Huang; Wen Yang; Zuliang Chen; Zengwei Lai; Jianwei Sun
Journal:  Chem Sci       Date:  2019-08-26       Impact factor: 9.825

4.  Electrochemical Vicinal Difluorination of Alkenes: Scalable and Amenable to Electron-Rich Substrates.

Authors:  Sayad Doobary; Alexi T Sedikides; Henry P Caldora; Darren L Poole; Alastair J J Lennox
Journal:  Angew Chem Int Ed Engl       Date:  2019-11-28       Impact factor: 15.336

Review 5.  Organic Electrochemistry: Molecular Syntheses with Potential.

Authors:  Cuiju Zhu; Nate W J Ang; Tjark H Meyer; Youai Qiu; Lutz Ackermann
Journal:  ACS Cent Sci       Date:  2021-03-09       Impact factor: 14.553

6.  A new hypervalent iodine(iii/v) oxidant and its application to the synthesis of 2H-azirines.

Authors:  Guangtao Zhang; Yuanxun Wang; Jun Xu; Jiyun Sun; Fengxia Sun; Yilin Zhang; Chenglin Zhang; Yunfei Du
Journal:  Chem Sci       Date:  2019-12-06       Impact factor: 9.825

7.  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

8.  Flow electrochemistry: a safe tool for fluorine chemistry.

Authors:  Bethan Winterson; Tim Rennigholtz; Thomas Wirth
Journal:  Chem Sci       Date:  2021-06-04       Impact factor: 9.825

9.  The "Green" Electrochemical Synthesis of Periodate.

Authors:  Sebastian Arndt; Dominik Weis; Kai Donsbach; Siegfried R Waldvogel
Journal:  Angew Chem Int Ed Engl       Date:  2020-04-15       Impact factor: 15.336

10.  Substituent-controlled, mild oxidative fluorination of iodoarenes: synthesis and structural study of aryl I(iii)- and I(v)-fluorides.

Authors:  Joel Häfliger; Cody Ross Pitts; Dustin Bornemann; Roland Käser; Nico Santschi; Julie Charpentier; Elisabeth Otth; Nils Trapp; René Verel; Hans Peter Lüthi; Antonio Togni
Journal:  Chem Sci       Date:  2019-06-05       Impact factor: 9.825
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