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Literature DB >> 30295976

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids.

Xiao-Ye Yu¹, Quan-Qing Zhao¹, Jun Chen¹, Jia-Rong Chen¹, Wen-Jing Xiao^1,2.

Abstract

A visible-light-driven, copper-catalyzed three-component radical cross-coupling of oxime esters, styrenes, and boronic acids has been developed. Key steps of this protocol involve catalytic generation of an iminyl radical from a redox-active oxime ester and subsequent C-C bond cleavage to generate a cyanoalkyl radical. Upon its addition to styrene, the newly formed benzylic radical undergoes coupling with a boronic-acid-derived ArCuII complex to achieve 1,1-diarylmethane-containing alkylnitriles.

Entities: Chemical

Keywords: copper; cross-coupling; photochemistry; radicals; synthetic methods

Year: 2018 PMID： 30295976 DOI： 10.1002/anie.201809820

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

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Cited

11 in total

Review 1. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Authors: Kitae Kwon; R Thomas Simons; Meganathan Nandakumar; Jennifer L Roizen
Journal: Chem Rev Date: 2021-10-08 Impact factor: 60.622

2. Deacylation-Aided C─H Alkylative Annulation through C─C Cleavage of Unstrained Ketones.

Authors: Xukai Zhou; Yan Xu; Guangbin Dong
Journal: Nat Catal Date: 2021-08-02

Review 3. Visible Light-Induced Transition Metal Catalysis.

Authors: Kelvin Pak Shing Cheung; Sumon Sarkar; Vladimir Gevorgyan
Journal: Chem Rev Date: 2021-10-08 Impact factor: 72.087

Review 4. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.

Authors: Chia-Yu Huang; Jianbin Li; Chao-Jun Li
Journal: Chem Sci Date: 2022-04-18 Impact factor: 9.969

5. Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades.

Authors: Lucrezia Angelini; Jacob Davies; Marco Simonetti; Laia Malet Sanz; Nadeem S Sheikh; Daniele Leonori
Journal: Angew Chem Int Ed Engl Date: 2019-03-12 Impact factor: 15.336

10. A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades.

Authors: Elizabeth M Dauncey; Shashikant U Dighe; James J Douglas; Daniele Leonori
Journal: Chem Sci Date: 2019-06-27 Impact factor: 9.825

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids.

Review 1. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

2. Deacylation-Aided C─H Alkylative Annulation through C─C Cleavage of Unstrained Ketones.

Review 3. Visible Light-Induced Transition Metal Catalysis.

Review 4. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.

5. Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades.

Review 6. Indolylboronic Acids: Preparation and Applications.

7. Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis.

8. Efficient one-pot green synthesis of tetrakis(acetonitrile)copper(i) complex in aqueous media.

Review 9. The emerging roles of N6-methyladenosine (m6A) deregulation in liver carcinogenesis.

10. A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades.

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids.

Review 1. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

2. Deacylation-Aided C─H Alkylative Annulation through C─C Cleavage of Unstrained Ketones.

Review 3. Visible Light-Induced Transition Metal Catalysis.

Review 4. Photocatalytic C(sp3) radical generation via C-H, C-C, and C-X bond cleavage.

5. Reaction of Nitrogen-Radicals with Organometallics Under Ni-Catalysis: N-Arylations and Amino-Functionalization Cascades.

Review 6. Indolylboronic Acids: Preparation and Applications.

7. Asymmetric three-component olefin dicarbofunctionalization enabled by photoredox and copper dual catalysis.

8. Efficient one-pot green synthesis of tetrakis(acetonitrile)copper(i) complex in aqueous media.

Review 9. The emerging roles of N6-methyladenosine (m6A) deregulation in liver carcinogenesis.

10. A dual photoredox-nickel strategy for remote functionalization via iminyl radicals: radical ring-opening-arylation, -vinylation and -alkylation cascades.

Review 4. Photocatalytic C(sp³) radical generation via C-H, C-C, and C-X bond cleavage.