Chain propagation determines the chemo- and regioselectivity of alkyl radical additions to C–O vs. C

Chain propagation determines the chemo- and regioselectivity of alkyl radical additions to C–O vs. C–C double bonds

Published:2020 Issue:3 Volume:11 Page:731-736
ISSN:2041-6520
Container-title:Chemical Science
language:en
Short-container-title:Chem. Sci.

Author:

Paulisch Tiffany O.¹²³⁴,Strieth-Kalthoff Felix¹²³⁴,Henkel Christian⁵⁶⁷⁴,Pitzer Lena¹²³⁴,Guldi Dirk M.⁵⁶⁷⁴^ORCID,Glorius Frank¹²³⁴^ORCID

Affiliation:

1. Westfälische Wilhelms-Universität Münster

2. Organisch-Chemisches Institut

3. 48149 Münster

4. Germany

5. Friedrich-Alexander-Universität Erlangen-Nürnberg

6. Department of Chemistry and Pharmacy

7. 91058 Erlangen

Abstract

Reversible radical addition followed by an irreversible electron transfer leads to regio- and chemoselectivity control of radical additions to π-systems.

Funder

Deutsche Forschungsgemeinschaft

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/SC/C9SC04846D

Reference56 articles.

1. The Design and Application of Free Radical Chain Reactions in Organic Synthesis. Part 1

2. The Design and Application of Free Radical Chain Reactions in Organic Synthesis. Part 2

3. Syntheses with Radicals?C?C Bond Formation via Organotin and Organomercury Compounds [New Synthetic Methods (52)]

4. Selectivity: A Key to Synthetic Efficiency

5. Formation of CC Bonds by Addition of Free Radicals to Alkenes

Cited by 9 articles. 订阅此论文施引文献订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献

1. Diastereoselective Construction of α‐Fluoroalkyl Cycloalkanols via Radical Alkylation of α‐Fluoroalkyl Ketones^†;Chinese Journal of Chemistry;2023-09-14

2. Mechanistic and kinetic studies of visible light photoredox reactions;Chemical Physics Reviews;2023-09-01

3. Direct Aroylation of Olefins through a Cobalt/Photoredox‐Catalyzed Decarboxylative and Dehydrogenative Coupling with α‐Oxo Acids;Chemistry – A European Journal;2022-11-21

4. Photocatalytic Addition Reactions of Ketene Silyl Acetals with Alkenes through Formation of α‐Carbonyl Radicals;Chemistry – An Asian Journal;2022-09-02

5. Two Paths to Oxidative C−H Amination Under Basic Conditions: A Theoretical Case Study Reveals Hidden Opportunities Provided by Electron Upconversion**;Chemistry – A European Journal;2022-08-31