Literature DB >> 24839171

Double C-F bond activation through β-fluorine elimination: nickel-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes.

Tomohiro Ichitsuka1, Takeshi Fujita, Tomohiro Arita, Junji Ichikawa.   

Abstract

The nickel-mediated [3+2] cycloaddition of 2-trifluoromethyl-1-alkenes with alkynes afforded fluorine-containing multi-substituted cyclopentadienes in a regioselective manner. This reaction involves the consecutive two C-F bond cleavage of a trifluoromethyl or a pentafluoroethyl group through β-fluorine elimination.
© 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Entities:  

Keywords:  CF bond activation; alkynes; cycloaddition; cyclopentadienes; fluoroalkenes; nickel

Year:  2014        PMID: 24839171     DOI: 10.1002/anie.201402695

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


  11 in total

1.  Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent.

Authors:  Yufan Liang; Gregory C Fu
Journal:  Angew Chem Int Ed Engl       Date:  2015-06-12       Impact factor: 15.336

2.  Photoredox Generation of Carbon-Centered Radicals Enables the Construction of 1,1-Difluoroalkene Carbonyl Mimics.

Authors:  Simon B Lang; Rebecca J Wiles; Christopher B Kelly; Gary A Molander
Journal:  Angew Chem Int Ed Engl       Date:  2017-10-24       Impact factor: 15.336

3.  When Weaker Can Be Tougher: The Role of Oxidation State (I) in P- vs N-Ligand-Derived Ni-Catalyzed Trifluoromethylthiolation of Aryl Halides.

Authors:  Indrek Kalvet; Qianqian Guo; Graham J Tizzard; Franziska Schoenebeck
Journal:  ACS Catal       Date:  2017-01-31       Impact factor: 13.084

4.  DFT Studies on Ni-Mediated C-F Cleavage for the Synthesis of Cyclopentadiene Derivatives.

Authors:  Wen-Jie Chen; Ruo-Nan Xu; Weimin Lin; Xuejiao Sun; Bin Wang; Qi-Hui Wu; Xin Huang
Journal:  Front Chem       Date:  2018-08-13       Impact factor: 5.221

5.  Ni-catalyzed migratory fluoro-alkenylation of unactivated alkyl bromides with gem-difluoroalkenes.

Authors:  Lu Zhou; Chuan Zhu; Peijia Bi; Chao Feng
Journal:  Chem Sci       Date:  2018-11-09       Impact factor: 9.825

6.  Selective single C-F bond arylation of trifluoromethylalkene derivatives.

Authors:  Luning Tang; Ze-Yao Liu; Wenzhi She; Chao Feng
Journal:  Chem Sci       Date:  2019-08-05       Impact factor: 9.825

7.  Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate.

Authors:  Can Liu; Ni Shen; Rui Shang
Journal:  Nat Commun       Date:  2022-01-17       Impact factor: 14.919

8.  Competing C-H and C-F bond activation reactions of a fluorinated olefin at Rh: a fluorido vinylidene complex as an intermediate in an unprecedented dehydrofluorination step.

Authors:  Maria Talavera; Thomas Braun
Journal:  Chem Sci       Date:  2022-01-12       Impact factor: 9.825

9.  Synergistic Pd/Cu-catalyzed enantioselective Csp2-F bond alkylation of fluoro-1,3-dienes with aldimine esters.

Authors:  Huimin Yu; Qinglong Zhang; Weiwei Zi
Journal:  Nat Commun       Date:  2022-05-05       Impact factor: 17.694

10.  Synthesis of gem-Difluoro Olefins through C-H Functionalization and β-fluoride Elimination Reactions.

Authors:  Zhen Yang; Mieke Möller; Rene M Koenigs
Journal:  Angew Chem Int Ed Engl       Date:  2020-02-21       Impact factor: 15.336

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