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Literature DB >> 24079447

Cobalt-catalyzed hydrofluorination of unactivated olefins: a radical approach of fluorine transfer.

Hiroki Shigehisa¹, Eriko Nishi, Mayu Fujisawa, Kou Hiroya.

Abstract

Catalytic hydrofluorination of olefins using a cobalt catalyst was developed. The exclusive Markovnikov selectivity, functional group tolerance, and scalability of this reaction make it an attractive protocol for the hydrofluorination of olefins. A preliminary mechanistic experiment showed the involvement of a radical intermediate.

Entities: Chemical

Mesh：

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Year: 2013 PMID： 24079447 DOI： 10.1021/ol402696h

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

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Cited

17 in total

1. Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

Authors: Jeishla L M Matos; Suhelen Vásquez-Céspedes; Jieyu Gu; Takuya Oguma; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2018-11-29 Impact factor: 15.419

2. Ph(i-PrO)SiH2: An Exceptional Reductant for Metal-Catalyzed Hydrogen Atom Transfers.

Authors: Carla Obradors; Ruben M Martinez; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2016-03-30 Impact factor: 15.419

3. Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.

Authors: Sophia L Shevick; Carla Obradors; Ryan A Shenvi
Journal: J Am Chem Soc Date: 2018-09-18 Impact factor: 15.419

4. Cobalt-Catalyzed Hydrogen-Atom Transfer Induces Bicyclizations that Tolerate Electron-Rich and Electron-Deficient Intermediate Alkenes.

Authors: Darius Vrubliauskas; Christopher D Vanderwal
Journal: Angew Chem Int Ed Engl Date: 2020-02-25 Impact factor: 15.336

5. Cobalt-Carbon Bonding in a Salen-Supported Cobalt(IV) Alkyl Complex Postulated in Oxidative MHAT Catalysis.

Authors: Conner V Wilson; Dongyoung Kim; Ajay Sharma; Reagan X Hooper; Rinaldo Poli; Brian M Hoffman; Patrick L Holland
Journal: J Am Chem Soc Date: 2022-06-03 Impact factor: 16.383

6. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

Authors: Stefan Andrew Harry; Michael Richard Xiang; Eric Holt; Andrea Zhu; Fereshte Ghorbani; Dhaval Patel; Thomas Lectka
Journal: Chem Sci Date: 2022-05-30 Impact factor: 9.969

Cobalt-catalyzed hydrofluorination of unactivated olefins: a radical approach of fluorine transfer.

1. Branch-Selective Addition of Unactivated Olefins into Imines and Aldehydes.

2. Ph(i-PrO)SiH2: An Exceptional Reductant for Metal-Catalyzed Hydrogen Atom Transfers.

3. Mechanistic Interrogation of Co/Ni-Dual Catalyzed Hydroarylation.

4. Cobalt-Catalyzed Hydrogen-Atom Transfer Induces Bicyclizations that Tolerate Electron-Rich and Electron-Deficient Intermediate Alkenes.

5. Cobalt-Carbon Bonding in a Salen-Supported Cobalt(IV) Alkyl Complex Postulated in Oxidative MHAT Catalysis.

6. Hydroxy-directed fluorination of remote unactivated C(sp³)-H bonds: a new age of diastereoselective radical fluorination.

7. Mn-, Fe-, and Co-Catalyzed Radical Hydrofunctionalizations of Olefins.

8. The direct anti-Markovnikov addition of mineral acids to styrenes.

9. Hydrofluorination of Alkynes Catalysed by Gold Bifluorides.

10. A practical and catalytic reductive olefin coupling.