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Literature DB >> 34109055

Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Abstract

The allylation reaction is a highly versatile transformation in chemical synthesis. While many elegant direct C(sp2)-H allylation reactions have been developed, the direct allylation of unactivated C(sp3)-H bonds is underdeveloped. By applying photoredox catalysis and a [1,5]-HAT process, herein we report a direct allylation of unactivated C(sp3)‒H bonds. This photocatalyzed transformation is tolerant of several functional groups in the amide and allylic chloride substrates. Various allyl-substituted amide products were obtained with good yields and high δ-selectivity.

Entities: Chemical Species

Keywords: Allylation; C(sp3)‒H; [1,5]-HAT; photocatalysis; radical; δ-selectivity

Year: 2019 PMID： 34109055 PMCID： PMC8186322 DOI： 10.1021/acscatal.9b00563

Source DB: PubMed Journal: ACS Catal Impact factor: 13.084

42 in total

Review 1. Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Authors: Jimmie D Weaver; Antonio Recio; Alexander J Grenning; Jon A Tunge
Journal: Chem Rev Date: 2011-01-14 Impact factor: 60.622

2. Catalytic enantioselective allylation of carbonyl compounds and imines.

Authors: Miguel Yus; José C González-Gómez; Francisco Foubelo
Journal: Chem Rev Date: 2011-09-16 Impact factor: 60.622

3. C-H functionalization in organic synthesis.

Authors: Huw M L Davies; Justin Du Bois; Jin-Quan Yu
Journal: Chem Soc Rev Date: 2011-03-10 Impact factor: 54.564

Review 4. Late-Stage Peptide Diversification by Position-Selective C-H Activation.

Authors: Wei Wang; Mélanie M Lorion; Jagrut Shah; Anant R Kapdi; Lutz Ackermann
Journal: Angew Chem Int Ed Engl Date: 2018-10-09 Impact factor: 15.336

Review 5. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

Authors: John C K Chu; Tomislav Rovis
Journal: Angew Chem Int Ed Engl Date: 2017-12-05 Impact factor: 15.336

6. Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade.

Authors: Wei Shu; Cristina Nevado
Journal: Angew Chem Int Ed Engl Date: 2017-01-18 Impact factor: 15.336

7. Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

Authors: Yang Yang; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2013-07-12 Impact factor: 15.419

8. Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Authors: Leah M Stateman; Kohki M Nakafuku; David A Nagib
Journal: Synthesis (Stuttg) Date: 2018-02-12 Impact factor: 3.157

9. Cross-coupling of aromatic bromides with allylic silanolate salts.

Authors: Scott E Denmark; Nathan S Werner
Journal: J Am Chem Soc Date: 2008-12-03 Impact factor: 15.419

10. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp³)-H bonds.

Authors: Xinxin Wu; Hong Zhang; Nana Tang; Zhen Wu; Dongping Wang; Meishan Ji; Yan Xu; Min Wang; Chen Zhu
Journal: Nat Commun Date: 2018-08-21 Impact factor: 14.919

8 in total

1. Aza-Heterocycles via Copper-Catalyzed, Remote C-H Desaturation of Amines.

Authors: Leah M Stateman; Ross M Dare; Alyson N Paneque; David A Nagib
Journal: Chem Date: 2021-11-16 Impact factor: 22.804

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

Review 3. 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

Remote Allylation of Unactivated C(sp³)-H Bonds Triggered by Photogenerated Amidyl Radicals.

Review 1. Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

2. Catalytic enantioselective allylation of carbonyl compounds and imines.

3. C-H functionalization in organic synthesis.

Review 4. Late-Stage Peptide Diversification by Position-Selective C-H Activation.

Review 5. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

6. Visible-Light-Mediated Remote Aliphatic C-H Functionalizations through a 1,5-Hydrogen Transfer Cascade.

7. Ligand-controlled palladium-catalyzed regiodivergent Suzuki-Miyaura cross-coupling of allylboronates and aryl halides.

8. Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

9. Cross-coupling of aromatic bromides with allylic silanolate salts.

10. Metal-free alcohol-directed regioselective heteroarylation of remote unactivated C(sp³)-H bonds.

1. Aza-Heterocycles via Copper-Catalyzed, Remote C-H Desaturation of Amines.

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

Review 3. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Review 4. Photoredox-Catalyzed C-H Functionalization Reactions.

5. TBAI-Catalyzed Oxidative Coupling of Benzyl Ketones to Synthesize 2,3-Diaryl-1,4-Diketones in Water.

6. Modular allylation of C(sp³)-H bonds by combining decatungstate photocatalysis and HWE olefination in flow.

7. Direct C-H Allylation of Unactivated Alkanes by Cooperative W/Cu Photocatalysis.

8. Transition-metal-free allylation of 2-azaallyls with allyl ethers through polar and radical mechanisms.

Review 1. Transition metal-catalyzed decarboxylative allylation and benzylation reactions.

Review 4. Late-Stage Peptide Diversification by Position-Selective C-H Activation.

Review 5. Complementary Strategies for Directed C(sp3 )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.

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

Review 3. Strategies to Generate Nitrogen-centered Radicals That May Rely on Photoredox Catalysis: Development in Reaction Methodology and Applications in Organic Synthesis.

Review 4. Photoredox-Catalyzed C-H Functionalization Reactions.

Review 5. Complementary Strategies for Directed C(sp³ )-H Functionalization: A Comparison of Transition-Metal-Catalyzed Activation, Hydrogen Atom Transfer, and Carbene/Nitrene Transfer.