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Literature DB >> 29755145

Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

Leah M Stateman¹, Kohki M Nakafuku¹, David A Nagib¹.

Abstract

The selective functionalization of remote C-H bonds via intramolecular hydrogen atom transfer (HAT) is transformative for organic synthesis. This radical-mediated strategy provides access to novel reactivity that is complementary to closed-shell pathways. As modern methods for mild generation of radicals are continually developed, inherent selectivity paradigms of HAT mechanisms offer unparalleled opportunities for developing new strategies for C-H functionalization. This review outlines the history, recent advances, and mechanistic underpinnings of intramolecular HAT as a guide to addressing ongoing challenges in this arena.

Entities: Chemical Disease Gene

Keywords: hydrogen atom transfer; nitrogen-centered radicals; oxygen-centered radicals; radicals; remote C–H functionalization

Year: 2018 PMID： 29755145 PMCID： PMC5940016 DOI： 10.1055/s-0036-1591930

Source DB: PubMed Journal: Synthesis (Stuttg) ISSN： 0039-7881 Impact factor: 3.157

90 in total

1. Remote oxidation of steroids by photolysis of attached benzophenone groups.

Authors: R Breslow; S Baldwin; T Flechtner; P Kalicky; S Liu; W Washburn
Journal: J Am Chem Soc Date: 1973-05-16 Impact factor: 15.419

2. Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation.

Authors: Takuma Hashimoto; Daisuke Hirose; Tsuyoshi Taniguchi
Journal: Angew Chem Int Ed Engl Date: 2014-02-02 Impact factor: 15.336

3. α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp³ )-H Functionalization of Ketones.

Authors: Heng Jiang; Armido Studer
Journal: Angew Chem Int Ed Engl Date: 2018-01-15 Impact factor: 15.336

4. Copper-catalyzed aliphatic C-H amination with an amidine moiety.

Authors: Hui Chen; Stephen Sanjaya; Yi-Feng Wang; Shunsuke Chiba
Journal: Org Lett Date: 2012-12-19 Impact factor: 6.005

Review 5. C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

Authors: Junichiro Yamaguchi; Atsushi D Yamaguchi; Kenichiro Itami
Journal: Angew Chem Int Ed Engl Date: 2012-08-06 Impact factor: 15.336

6. Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids.

Authors: Bérénice C Lemercier; Joshua G Pierce
Journal: Org Lett Date: 2015-09-02 Impact factor: 6.005

7. Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems.

Authors: Cosme G Francisco; Antonio J Herrera; Ernesto Suárez
Journal: J Org Chem Date: 2003-02-07 Impact factor: 4.354

8. Visible light photoredox-controlled reactions of N-radicals and radical ions.

Authors: Jia-Rong Chen; Xiao-Qiang Hu; Liang-Qiu Lu; Wen-Jing Xiao
Journal: Chem Soc Rev Date: 2016-02-03 Impact factor: 54.564

9. Guided desaturation of unactivated aliphatics.

Authors: Ana-Florina Voica; Abraham Mendoza; Will R Gutekunst; Jorge Otero Fraga; Phil S Baran
Journal: Nat Chem Date: 2012-07-08 Impact factor: 24.427

10. Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

Authors: Elizabeth M Dauncey; Sara P Morcillo; James J Douglas; Nadeem S Sheikh; Daniele Leonori
Journal: Angew Chem Int Ed Engl Date: 2017-12-04 Impact factor: 15.336

59 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

Remote C-H Functionalization via Selective Hydrogen Atom Transfer.

1. Remote oxidation of steroids by photolysis of attached benzophenone groups.

2. Direct synthesis of 1,4-diols from alkenes by iron-catalyzed aerobic hydration and C-H hydroxylation.

3. α-Aminoxy-Acid-Auxiliary-Enabled Intermolecular Radical γ-C(sp³ )-H Functionalization of Ketones.

4. Copper-catalyzed aliphatic C-H amination with an amidine moiety.

Review 5. C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals.

6. Synthesis of 1,4,2-Oxathiazoles via Oxidative Cyclization of Thiohydroximic Acids.

7. Intramolecular hydrogen abstraction reaction promoted by N-radicals in carbohydrates. Synthesis of chiral 7-oxa-2-azabicyclo[2.2.1]heptane and 8-oxa-6-azabicyclo[3.2.1]octane ring systems.

8. Visible light photoredox-controlled reactions of N-radicals and radical ions.

9. Guided desaturation of unactivated aliphatics.

10. Photoinduced Remote Functionalisations by Iminyl Radical Promoted C-C and C-H Bond Cleavage Cascades.

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

2. Merging Photochemistry with Electrochemistry: Functional-Group Tolerant Electrochemical Amination of C(sp³ )-H Bonds.

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

Review 4. Biocatalytic hydrogen atom transfer: an invigorating approach to free-radical reactions.

5. Aliphatic Radical Relay Heck Reaction at Unactivated C(sp³ )-H Sites of Alcohols.

6. Enantioselective Intermolecular Radical C-H Amination.

7. δ-C-H Mono- and Dihalogenation of Alcohols.

8. Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay.

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

10. Visible-Light-Induced Palladium-Catalyzed Generation of Aryl Radicals from Aryl Triflates.