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Literature DB >> 27240116

Electrochemical C-H/N-H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles.

Zhong-Wei Hou¹, Zhong-Yi Mao¹, Huai-Bo Zhao¹, Yared Yohannes Melcamu¹, Xin Lu², Jinshuai Song^1,3, Hai-Chao Xu⁴.

Abstract

Indoles and azaindoles are among the most important heterocycles because of their prevalence in nature and their broad utility in pharmaceutical industry. Reported herein is an unprecedented noble-metal- and oxidant-free electrochemical method for the coupling of (hetero)arylamines with tethered alkynes to synthesize highly functionalized indoles, as well as the more challenging azaindoles.

Entities: Chemical

Keywords: electrochemistry; heterocycles; indoles; radicals; redox chemistry

Year: 2016 PMID： 27240116 DOI： 10.1002/anie.201602616

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

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Cited

14 in total

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

Authors: Ming Yan; Yu Kawamata; Phil S Baran
Journal: Chem Rev Date: 2017-10-09 Impact factor: 60.622

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

Review 3. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

Authors: Philip R D Murray; James H Cox; Nicholas D Chiappini; Casey B Roos; Elizabeth A McLoughlin; Benjamin G Hejna; Suong T Nguyen; Hunter H Ripberger; Jacob M Ganley; Elaine Tsui; Nick Y Shin; Brian Koronkiewicz; Guanqi Qiu; Robert R Knowles
Journal: Chem Rev Date: 2021-11-23 Impact factor: 60.622

4. 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

Review 5. Electrifying Organic Synthesis.

Authors: Anton Wiebe; Tile Gieshoff; Sabine Möhle; Eduardo Rodrigo; Michael Zirbes; Siegfried R Waldvogel
Journal: Angew Chem Int Ed Engl Date: 2018-03-07 Impact factor: 15.336

Electrochemical C-H/N-H Functionalization for the Synthesis of Highly Functionalized (Aza)indoles.

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.

Review 3. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

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

Review 5. Electrifying Organic Synthesis.

6. Polysubstituted ferrocenes as tunable redox mediators.

7. Dehydrogenative reagent-free annulation of alkenes with diols for the synthesis of saturated O-heterocycles.

8. External oxidant-free electrooxidative [3 + 2] annulation between phenol and indole derivatives.

9. Facile Electrochemical Intramolecular Amination of Urea-Tethered Terminal Alkenes for the Synthesis of Cyclic Ureas.

10. Electrochemical oxidation induced selective tyrosine bioconjugation for the modification of biomolecules.