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Literature DB >> 29446188

Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines.

Nengneng Zhou¹, Xiang-Ai Yuan², Yue Zhao¹, Jin Xie¹, Chengjian Zhu^1,3.

Abstract

The first catalytic inverse hydroboration of imines with N-heterocyclic carbene (NHC) boranes has been realized by means of cooperative organocatalysis and photocatalysis. This catalytic combination provides a promising platform for promoting NHC-boryl radical chemistry under sustainable and radical-initiator-free conditions. The highly important functional-group compatibility and possible application in late-stage hydroborations represent an important step forward to an enhanced α-amino organoboron library.

Entities: Chemical Disease

Keywords: C−B coupling; hydroboration; imines; photochemistry; radicals

Year: 2018 PMID： 29446188 DOI： 10.1002/anie.201800421

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

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Cited

7 in total

Review 1. 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

2. A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

Authors: Muliang Zhang; Jin Xie; Chengjian Zhu
Journal: Nat Commun Date: 2018-08-29 Impact factor: 14.919

3. Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

Authors: Shi-Chao Ren; Feng-Lian Zhang; Ai-Qing Xu; Yinuo Yang; Min Zheng; Xiaoguo Zhou; Yao Fu; Yi-Feng Wang
Journal: Nat Commun Date: 2019-04-29 Impact factor: 14.919

7. DFT Investigation of Hydrogen Atom Abstraction from NHC-Boranes by Methyl, Ethyl and Cyanomethyl Radicals-Composition and Correlation Analysis of Kinetic Barriers.

Authors: Hong-Jie Qu; Lang Yuan; Cai-Xin Jia; Hai-Tao Yu; Hui Xu
Journal: Molecules Date: 2020-10-01 Impact factor: 4.411

7 in total

Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines.

Review 1. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

2. A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

3. Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

4. Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC-boranes.

5. Highly selective single and multiple deuteration of unactivated C(sp³)-H bonds.

6. Enantioselective Copper-Catalyzed sp²/sp³ Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

7. DFT Investigation of Hydrogen Atom Abstraction from NHC-Boranes by Methyl, Ethyl and Cyanomethyl Radicals-Composition and Correlation Analysis of Kinetic Barriers.

Synergistic Photoredox Catalysis and Organocatalysis for Inverse Hydroboration of Imines.

Review 1. Photochemical and Electrochemical Applications of Proton-Coupled Electron Transfer in Organic Synthesis.

2. A general deoxygenation approach for synthesis of ketones from aromatic carboxylic acids and alkenes.

3. Regioselective radical α-borylation of α,β-unsaturated carbonyl compounds for direct synthesis of α-borylcarbonyl molecules.

4. Photoinduced successive oxidative ring-opening and borylation of indolizines with NHC-boranes.

5. Highly selective single and multiple deuteration of unactivated C(sp3)-H bonds.

6. Enantioselective Copper-Catalyzed sp2/sp3 Diborylation of 1-Chloro-1-Trifluoromethylalkenes.

7. DFT Investigation of Hydrogen Atom Abstraction from NHC-Boranes by Methyl, Ethyl and Cyanomethyl Radicals-Composition and Correlation Analysis of Kinetic Barriers.

5. Highly selective single and multiple deuteration of unactivated C(sp³)-H bonds.

6. Enantioselective Copper-Catalyzed sp²/sp³ Diborylation of 1-Chloro-1-Trifluoromethylalkenes.