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Literature DB >> 28139930

Synthesis of gem-Difluoroallylboronates via FeCl₂-Catalyzed Boration/β-Fluorine Elimination of Trifluoromethyl Alkenes.

Yang Liu¹, Yuhan Zhou¹, Yilong Zhao¹, Jingping Qu¹.

Abstract

The first ferrous chloride catalyzed boration/β-fluorine elimination of trifluoromethyl alkenes is described. Thus, a full range of gem-difluoroallylboronates were obtained in high yield under mild conditions. As an important fluorinated building block, gem-difluoroallylboronate can be readily converted into diverse difluoro-substituted species.

Entities: Chemical

Year: 2017 PMID： 28139930 DOI： 10.1021/acs.orglett.7b00168

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

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Cited

14 in total

1. Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis.

Authors: Rebecca J Wiles; James P Phelan; Gary A Molander
Journal: Chem Commun (Camb) Date: 2019-06-14 Impact factor: 6.222

2. 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

3. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

Authors: Sota Akiyama; Koji Kubota; Malte S Mikus; Paulo H S Paioti; Filippo Romiti; Qinghe Liu; Yuebiao Zhou; Amir H Hoveyda; Hajime Ito
Journal: Angew Chem Int Ed Engl Date: 2019-07-16 Impact factor: 15.336

4. Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.

Authors: Jichao Xiao; John Montgomery
Journal: ACS Catal Date: 2022-02-03 Impact factor: 13.700

5. Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

Authors: Carla Saunders; Mohammad B Khaled; Jimmie D Weaver; Dean J Tantillo
Journal: J Org Chem Date: 2018-02-26 Impact factor: 4.354

6. Chemoselective catalytic hydrodefluorination of trifluoromethylalkenes towards mono-/gem-di-fluoroalkenes under metal-free conditions.

Authors: Jingjing Zhang; Jin-Dong Yang; Jin-Pei Cheng
Journal: Nat Commun Date: 2021-05-14 Impact factor: 14.919

Synthesis of gem-Difluoroallylboronates via FeCl₂-Catalyzed Boration/β-Fluorine Elimination of Trifluoromethyl Alkenes.

1. Metal-free defluorinative arylation of trifluoromethyl alkenes via photoredox catalysis.

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

3. Catalytic Enantioselective Synthesis of Allylic Boronates Bearing a Trisubstituted Alkenyl Fluoride and Related Derivatives.

4. Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes.

5. Prediction of ¹⁹F NMR Chemical Shifts for Fluorinated Aromatic Compounds.

6. Chemoselective catalytic hydrodefluorination of trifluoromethylalkenes towards mono-/gem-di-fluoroalkenes under metal-free conditions.

7. Rapid access to diverse, trifluoromethyl-substituted alkenes using complementary strategies.

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

9. Photoredox-mediated hydroalkylation and hydroarylation of functionalized olefins for DNA-encoded library synthesis.

Review 10. Recent Advances in the Construction of Fluorinated Organoboron Compounds.