Literature DB >> 28585741

Synthesis and Reactivity of Fluoroalkyl Copper Complexes by the Oxycupration of Tetrafluoroethylene.

Masato Ohashi1, Takuya Adachi1, Naoyoshi Ishida1, Kotaro Kikushima1, Sensuke Ogoshi1.   

Abstract

The copper(I)-mediated generation of -OCF2 CF2 - moieties by the oxycupration of tetrafluoroethylene (TFE) using either copper aryloxides or alkoxides is disclosed. The key intermediates, 2-aryloxy-1,1,2,2-tetrafluoroethyl and 2-alkoxy-1,1,2,2-tetrafluoroethyl copper complexes, were obtained from the reaction of the corresponding aryloxy and alkoxy copper complexes with TFE, and their structures in solution and in the solid state were unambiguously determined by multinuclear NMR spectroscopy and X-ray diffraction analysis. These copper complexes subsequently reacted with aryl iodides (ArI) to afford ROCF2 CF2 Ar (R=aryl or alkyl) in high yields.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  copper; ethers; reaction mechanisms; structure elucidation; synthetic methods

Year:  2017        PMID: 28585741     DOI: 10.1002/anie.201703923

Source DB:  PubMed          Journal:  Angew Chem Int Ed Engl        ISSN: 1433-7851            Impact factor:   15.336


  5 in total

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Authors:  Brendan J Graziano; Thais R Scott; Matthew V Vollmer; Michael J Dorantes; Victor G Young; Eckhard Bill; Laura Gagliardi; Connie C Lu
Journal:  Chem Sci       Date:  2022-05-05       Impact factor: 9.969

2.  Use of trifluoroacetaldehyde N-tfsylhydrazone as a trifluorodiazoethane surrogate and its synthetic applications.

Authors:  Xinyu Zhang; Zhaohong Liu; Xiangyu Yang; Yuanqing Dong; Matteo Virelli; Giuseppe Zanoni; Edward A Anderson; Xihe Bi
Journal:  Nat Commun       Date:  2019-01-17       Impact factor: 14.919

3.  Synthesis of aryl 2-bromo-2-chloro-1,1-difluoroethyl ethers through the base-mediated reaction between phenols and halothane.

Authors:  Yukiko Karuo; Ayaka Kametani; Atsushi Tarui; Kazuyuki Sato; Kentaro Kawai; Masaaki Omote
Journal:  Beilstein J Org Chem       Date:  2021-01-11       Impact factor: 2.883

4.  Practical tetrafluoroethylene fragment installation through a coupling reaction of (1,1,2,2-tetrafluorobut-3-en-1-yl)zinc bromide with various electrophiles.

Authors:  Ken Tamamoto; Shigeyuki Yamada; Tsutomu Konno
Journal:  Beilstein J Org Chem       Date:  2018-09-11       Impact factor: 2.883

5.  Controllable double CF2-insertion into sp2 C-Cu bond using TMSCF3: a facile access to tetrafluoroethylene-bridged structures.

Authors:  Qiqiang Xie; Ziyue Zhu; Lingchun Li; Chuanfa Ni; Jinbo Hu
Journal:  Chem Sci       Date:  2019-11-11       Impact factor: 9.825

  5 in total

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