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Literature DB >> 30861204

Electrochemical and Scalable Dehydrogenative C(sp³ )-H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow.

Pavlo Nikolaienko¹, Marc Jentsch², Ajit P Kale¹, Yunfei Cai¹, Magnus Rueping^1,2.

Abstract

A hydrogen atom transfer-directed electrochemical intramolecular C-H amination has been developed in which the N-radical species are generated at the anode, and the base required for the reaction is generated at the cathode. A broad range of valuable pyrrolidines were prepared in good yields and with high chemoselectivity. The reaction was easily scaled up in both batch and continuous flow systems.

Entities: Chemical Species

Keywords: 1,5-HAT; amination; electrosynthesis; flow electrolysis; pyrrolidines

Year: 2019 PMID： 30861204 DOI： 10.1002/chem.201806092

Source DB: PubMed Journal: Chemistry ISSN： 0947-6539 Impact factor: 5.236

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Cited

5 in total

1. Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Authors: Melanie A Short; J Miles Blackburn; Jennifer L Roizen
Journal: Synlett Date: 2019-11-27 Impact factor: 2.454

Review 2. 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

Electrochemical and Scalable Dehydrogenative C(sp³ )-H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow.

1. Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

3. Ritter-type amination of C(sp³)-H bonds enabled by electrochemistry with SO₄².

Review 4. Reproducibility in Electroorganic Synthesis-Myths and Misunderstandings.

5. Transition-metal-free C(sp³)-H/C(sp³)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines.

Electrochemical and Scalable Dehydrogenative C(sp3 )-H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow.

1. Modifying Positional Selectivity in C-H Functionalization Reactions with Nitrogen-Centered Radicals: Generalizable Approaches to 1,6-Hydrogen-Atom Transfer Processes.

Review 2. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

3. Ritter-type amination of C(sp3)-H bonds enabled by electrochemistry with SO42.

Review 4. Reproducibility in Electroorganic Synthesis-Myths and Misunderstandings.

5. Transition-metal-free C(sp3)-H/C(sp3)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines.

Electrochemical and Scalable Dehydrogenative C(sp³ )-H Amination via Remote Hydrogen Atom Transfer in Batch and Continuous Flow.

3. Ritter-type amination of C(sp³)-H bonds enabled by electrochemistry with SO₄².

5. Transition-metal-free C(sp³)-H/C(sp³)-H dehydrogenative coupling of saturated heterocycles with N-benzyl imines.