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Literature DB >> 29022709

Directed γ-C(sp³)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis.

Dian-Feng Chen¹, John C K Chu², Tomislav Rovis¹.

Abstract

Visible light photoredox catalysis enables direct γ- C(sp3)-H alkylation of saturated aliphatic carbonyl compounds. Electron-deficient alkenes are used as the coupling partners in this reaction. Distinguished site selectivity is controlled by the predominant 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

Entities: Chemical Disease Species

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Year: 2017 PMID： 29022709 PMCID： PMC5851452 DOI： 10.1021/jacs.7b09306

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

27 in total

1. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

Authors: B V Subba Reddy; Leleti Rajender Reddy; E J Corey
Journal: Org Lett Date: 2006-07-20 Impact factor: 6.005

2. Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Johannes Richers; Michael Heilmann; Markus Drees; Konrad Tiefenbacher
Journal: Org Lett Date: 2016-12-05 Impact factor: 6.005

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

Authors: Jian He; Masayuki Wasa; Kelvin S L Chan; Qian Shao; Jin-Quan Yu
Journal: Chem Rev Date: 2016-12-02 Impact factor: 60.622

4. Amide-directed photoredox-catalysed C-C bond formation at unactivated sp³ C-H bonds.

Authors: John C K Chu; Tomislav Rovis
Journal: Nature Date: 2016-10-12 Impact factor: 49.962

Review 5. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

Authors: Christopher K Prier; Danica A Rankic; David W C MacMillan
Journal: Chem Rev Date: 2013-03-19 Impact factor: 60.622

6. Copper-Catalyzed Bromination of C(sp³ )-H Bonds Distal to Functional Groups.

Authors: Tao Liu; Michael C Myers; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2016-11-29 Impact factor: 15.336

7. γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

Authors: Tao Liu; Tian-Sheng Mei; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2015-04-30 Impact factor: 15.419

8. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

Authors: Ke Chen; Jeremy M Richter; Phil S Baran
Journal: J Am Chem Soc Date: 2008-05-16 Impact factor: 15.419

9. Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.

Authors: Fang-Lin Zhang; Kai Hong; Tuan-Jie Li; Hojoon Park; Jin-Quan Yu
Journal: Science Date: 2016-01-15 Impact factor: 47.728

10. Triiodide-Mediated δ-Amination of Secondary C-H Bonds.

Authors: Ethan A Wappes; Stacy C Fosu; Trevor C Chopko; David A Nagib
Journal: Angew Chem Int Ed Engl Date: 2016-07-07 Impact factor: 15.336

30 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

Directed γ-C(sp³)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis.

1. Novel acetoxylation and C-C coupling reactions at unactivated positions in alpha-amino acid derivatives.

2. Synthesis of Lactones via C-H Functionalization of Nonactivated C(sp³)-H Bonds.

3. Palladium-Catalyzed Transformations of Alkyl C-H Bonds.

4. Amide-directed photoredox-catalysed C-C bond formation at unactivated sp³ C-H bonds.

Review 5. Visible light photoredox catalysis with transition metal complexes: applications in organic synthesis.

6. Copper-Catalyzed Bromination of C(sp³ )-H Bonds Distal to Functional Groups.

7. γ,δ,ε-C(sp(3))-H Functionalization through Directed Radical H-Abstraction.

8. 1,3-Diol synthesis via controlled, radical-mediated C-H functionalization.

9. Organic chemistry. Functionalization of C(sp3)-H bonds using a transient directing group.

10. Triiodide-Mediated δ-Amination of Secondary C-H Bonds.

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

2. General, Mild, and Selective Method for Desaturation of Aliphatic Amines.

3. Photoredox-Catalyzed Site-Selective α-C(sp³ )-H Alkylation of Primary Amine Derivatives.

4. Identifying Amidyl Radicals for Intermolecular C-H Functionalizations.

5. Regioselective Alkylative Cross-Coupling of Remote Unactivated C(sp³)-H Bonds.

6. Sulfamate Esters Guide C(3)-Selective Xanthylation of Alkanes.

7. A General Strategy for Aliphatic C-H Functionalization Enabled by Organic Photoredox Catalysis.

8. Sulfamate Esters Guide Selective Radical-Mediated Chlorination of Aliphatic C-H Bonds.

9. Chiral piperidines from acyclic amines via enantioselective, radical-mediated δ C-H cyanation.

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