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Literature DB >> 27341676

The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling.

Ryutaro Hayashi¹, Akihiro Shimizu¹, Jun-Ichi Yoshida¹.

Abstract

Electrochemical oxidation of toluene derivatives in the presence of a sulfilimine gave benzylaminosulfonium ions as stabilized benzyl cation pools, which reacted with subsequently added aromatic nucleophiles to give the corresponding cross-coupling products. The transformation serves as a powerful metal- and chemical-oxidant-free method for benzylic C-H/aromatic C-H cross-coupling. The method has been successfully applied to synthesis of TP27, an inhibitor of PTPase.

Entities: Chemical

Mesh：

Substances：
Carbon
Hydrogen
Benzene

Year: 2016 PMID： 27341676 DOI： 10.1021/jacs.6b05273

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

15 in total

1. Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

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2. N-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C-H Functionalization.

Authors: Mohammad Rafiee; Fei Wang; Damian P Hruszkewycz; Shannon S Stahl
Journal: J Am Chem Soc Date: 2017-12-19 Impact factor: 15.419

3. Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

Authors: Bill J Motsch; Sarah E Wengryniuk
Journal: Org Lett Date: 2022-08-08 Impact factor: 6.072

4. Radical C(sp3)-H functionalization and cross-coupling reactions.

Authors: Dung L Golden; Sung-Eun Suh; Shannon S Stahl
Journal: Nat Rev Chem Date: 2022-05-17 Impact factor: 34.571

5. Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators.

Authors: Fei Wang; Shannon S Stahl
Journal: Acc Chem Res Date: 2020-02-12 Impact factor: 22.384

6. An Easy-to-Machine Electrochemical Flow Microreactor: Efficient Synthesis of Isoindolinone and Flow Functionalization.

Authors: Ana A Folgueiras-Amador; Kai Philipps; Sébastien Guilbaud; Jarno Poelakker; Thomas Wirth
Journal: Angew Chem Int Ed Engl Date: 2017-11-02 Impact factor: 15.336

The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling.

1. Synthetic Organic Electrochemical Methods Since 2000: On the Verge of a Renaissance.

2. N-Hydroxyphthalimide-Mediated Electrochemical Iodination of Methylarenes and Comparison to Electron-Transfer-Initiated C-H Functionalization.

3. Site-Selective Synthesis of N-Benzyl 2,4,6-Collidinium Salts by Electrooxidative C-H Functionalization.

4. Radical C(sp3)-H functionalization and cross-coupling reactions.

5. Electrochemical Oxidation of Organic Molecules at Lower Overpotential: Accessing Broader Functional Group Compatibility with Electron-Proton Transfer Mediators.

6. An Easy-to-Machine Electrochemical Flow Microreactor: Efficient Synthesis of Isoindolinone and Flow Functionalization.

7. Electrochemical oxidative decarboxylation and 1,2-aryl migration towards the synthesis of 1,2-diaryl ethers.

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

9. Electrocatalytic redox neutral [3 + 2] annulation of N-cyclopropylanilines and alkenes.

10. Aziridine synthesis by coupling amines and alkenes via an electrogenerated dication.