Literature DB >> 11421787

Nickel(0)-catalyzed fluoroalkylation of alkenes, alkynes, and aromatics with perfluoroalkyl chlorides.

X T Huang1, Q Y Chen.   

Abstract

Treatment of perfluoroalkyl chlorides (R(F)Cl) with alkenes, alkynes, or aromatics in the presence of 0.1 equiv of nickel dichloride, 1.5 equiv of zinc powder, and 0.4 equiv of triphenylphosphine in DMF at 95-100 degrees C for 6-8 h give the corresponding perfluoroalkylated products in good yields. A single electron-transfer mechanism is suggested.

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Year:  2001        PMID: 11421787     DOI: 10.1021/jo010178j

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

Review 1.  Recent advances in transition metal-catalyzed Csp(2)-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation.

Authors:  Grégory Landelle; Armen Panossian; Sergiy Pazenok; Jean-Pierre Vors; Frédéric R Leroux
Journal:  Beilstein J Org Chem       Date:  2013-11-15       Impact factor: 2.883

2.  Highly selective nickel-catalyzed gem-difluoropropargylation of unactivated alkylzinc reagents.

Authors:  Lun An; Chang Xu; Xingang Zhang
Journal:  Nat Commun       Date:  2017-11-13       Impact factor: 14.919

3.  Difluoromethylation of (hetero)aryl chlorides with chlorodifluoromethane catalyzed by nickel.

Authors:  Chang Xu; Wen-Hao Guo; Xu He; Yin-Long Guo; Xue-Ying Zhang; Xingang Zhang
Journal:  Nat Commun       Date:  2018-03-21       Impact factor: 14.919

4.  Catalytic Hydrodifluoroalkylation of Unactivated Olefins.

Authors:  Wen-Jun Yue; Craig S Day; Adrian J Brenes Rucinski; Ruben Martin
Journal:  Org Lett       Date:  2022-07-10       Impact factor: 6.072

5.  Modular synthesis of α-fluorinated arylmethanes via desulfonylative cross-coupling.

Authors:  Masakazu Nambo; Jacky C-H Yim; Luiza B O Freitas; Yasuyo Tahara; Zachary T Ariki; Yuuki Maekawa; Daisuke Yokogawa; Cathleen M Crudden
Journal:  Nat Commun       Date:  2019-10-04       Impact factor: 14.919

  5 in total

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