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Literature DB >> 31793156

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides.

Ke-Jin Jiao¹, Dong Liu¹, Hong-Xing Ma^1,2, Hui Qiu¹, Ping Fang¹, Tian-Sheng Mei¹.

Abstract

A highly regioselective Ni-catalyzed electrochemical reductive relay cross-coupling between an aryl halide and an alkyl halide has been developed in an undivided cell. Various functional groups are tolerated under these mild reaction conditions, which provides an alternative approach for the synthesis of 1,1-diarylalkanes.

Entities: Chemical

Keywords: arenes; cross-coupling; electrochemistry; nickel; reaction mechanisms

Year: 2019 PMID： 31793156 DOI： 10.1002/anie.201912753

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

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Cited

12 in total

1. Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

Authors: David J Charboneau; Haotian Huang; Emily L Barth; Cameron C Germe; Nilay Hazari; Brandon Q Mercado; Mycah R Uehling; Susan L Zultanski
Journal: J Am Chem Soc Date: 2021-11-30 Impact factor: 15.419

2. Dinickel Catalyzed Vinylidene-Alkene Cyclization Reactions.

Authors: Talia J Steiman; Annah E Kalb; James C Coombs; Justin K Kirkland; Hector Torres; Daniel H Ess; Christopher Uyeda
Journal: ACS Catal Date: 2021-11-15 Impact factor: 13.700

Review 3. Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

Authors: David J Charboneau; Nilay Hazari; Haotian Huang; Mycah R Uehling; Susan L Zultanski
Journal: J Org Chem Date: 2022-06-07 Impact factor: 4.198

4. Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

Authors: Jiang Wang; Megan E Hoerrner; Mary P Watson; Daniel J Weix
Journal: Angew Chem Int Ed Engl Date: 2020-06-05 Impact factor: 15.336

9. Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated via C(sp³)-H activation.

Authors: Zhuo Wu; Hang Jiang; Yanghui Zhang
Journal: Chem Sci Date: 2021-05-19 Impact factor: 9.825

10. Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO₂.

Authors: Guo-Quan Sun; Wei Zhang; Li-Li Liao; Li Li; Zi-Hao Nie; Jin-Gui Wu; Zhen Zhang; Da-Gang Yu
Journal: Nat Commun Date: 2021-12-06 Impact factor: 14.919

Nickel-Catalyzed Electrochemical Reductive Relay Cross-Coupling of Alkyl Halides to Aryl Halides.

1. Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling.

2. Dinickel Catalyzed Vinylidene-Alkene Cyclization Reactions.

Review 3. Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations.

4. Nickel-Catalyzed Synthesis of Dialkyl Ketones from the Coupling of N-Alkyl Pyridinium Salts with Activated Carboxylic Acids.

5. Site-Selective C-H alkylation of Complex Arenes by a Two-Step Aryl Thianthrenation-Reductive Alkylation Sequence.

6. Nickela-electrocatalyzed Mild C-H Alkylations at Room Temperature.

7. Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds.

8. Nickel-catalyzed migratory alkyl-alkyl cross-coupling reaction.

9. Pd-catalyzed cross-electrophile Coupling/C-H alkylation reaction enabled by a mediator generated via C(sp³)-H activation.

10. Nickel-catalyzed electrochemical carboxylation of unactivated aryl and alkyl halides with CO₂.