Literature DB >> 28857377

Stereoselective Synthesis of Z Fluoroalkenes through Copper-Catalyzed Hydrodefluorination of gem-Difluoroalkenes with Water.

Jiefeng Hu1, Xiaowei Han1,2, Yu Yuan2, Zhuangzhi Shi1.   

Abstract

A copper catalytic system was established for the stereoselective hydrodefluorination of gem-difluoroalkenes through C-F activation to synthesize various Z fluoroalkenes. H2 O is used as the hydrogen source for the fluorine acceptor moiety. This mild catalytic system shows good-functional group compatibility, accepting a range of carbonyls as precursors to the gem-difluoroalkenes, including aliphatic, aromatic, and α,β-unsaturated aldehydes and even ketones. It serves as a powerful synthetic method for the late-stage modification of complex compounds.
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  Z selectivity; copper; fluorine; fluoroalkanes; hydrodefluorination

Year:  2017        PMID: 28857377     DOI: 10.1002/anie.201708224

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


  8 in total

1.  Gold-Catalyzed Hydrofluorination of Electron-Deficient Alkynes: Stereoselective Synthesis of β-Fluoro Michael Acceptors.

Authors:  Thomas J O'Connor; F Dean Toste
Journal:  ACS Catal       Date:  2018-06-04       Impact factor: 13.084

2.  Recent Advances in Transition Metal-Catalyzed Functionalization of gem-Difluoroalkenes.

Authors:  Suvajit Koley; Ryan A Altman
Journal:  Isr J Chem       Date:  2020-03-10       Impact factor: 3.333

3.  Catalyzing the Hydrodefluorination of CF3-Substituted Alkenes by PhSiH3. H• Transfer from a Nickel Hydride.

Authors:  Chengbo Yao; Shuai Wang; Jack Norton; Matthew Hammond
Journal:  J Am Chem Soc       Date:  2020-01-24       Impact factor: 15.419

4.  Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination.

Authors:  Thomas J O'Connor; Binh Khanh Mai; Jordan Nafie; Peng Liu; F Dean Toste
Journal:  J Am Chem Soc       Date:  2021-08-16       Impact factor: 16.383

5.  Silver-catalyzed synthesis of β-fluorovinylphosphonates by phosphonofluorination of aromatic alkynes.

Authors:  Yajing Zhang; Qingshan Tian; Guozhu Zhang; Dayong Zhang
Journal:  Beilstein J Org Chem       Date:  2020-12-18       Impact factor: 2.883

Review 6.  Recent Advances in the Construction of Fluorinated Organoboron Compounds.

Authors:  Xingxing Ma; Zhijie Kuang; Qiuling Song
Journal:  JACS Au       Date:  2021-12-30

7.  Ligand-controlled regioselective and chemodivergent defluorinative functionalization of gem-difluorocyclopropanes with simple ketones.

Authors:  Leiyang Lv; Huijun Qian; Yangyang Ma; Shiqing Huang; Xiaoyu Yan; Zhiping Li
Journal:  Chem Sci       Date:  2021-11-08       Impact factor: 9.825

8.  Arylation of gem-difluoroalkenes using a Pd/Cu Co-catalytic system that avoids β-fluoride elimination.

Authors:  Kedong Yuan; Taisiia Feoktistova; Paul Ha-Yeon Cheong; Ryan A Altman
Journal:  Chem Sci       Date:  2020-11-25       Impact factor: 9.825

  8 in total

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