scholarly journals Cascades, Catalysis and Chiral Ligand Control with SmI2; The Rebirth of a Reagent

2020 ◽  
Vol 74 (1) ◽  
pp. 18-22
Author(s):  
Áron Péter ◽  
David J. Procter
Keyword(s):  
Electron Transfer ◽  
Cascade Reactions ◽  
Single Electron ◽  
Radical Reactions ◽  
Chiral Ligand ◽  
Single Electron Transfer ◽  
Recent Developments ◽  
Radical Cascade

This review focuses on recent developments from our laboratory in the field of radical reactions mediated by the archetypal reductive single electron transfer (SET) reagent, SmI2. Namely, we have expanded the scope of reducible carbonyl moieties to esters and amides and have exploited the resultant ketyl radicals in radical cascade reactions that generate unprecedented scaffolds. Moreover, we have taken the first steps to address the long-standing challenges of catalysis and chiral ligand control associated with the reagent.

scholarly journals Chiral Nitroarenes as Enantioselective Single-Electron-Transfer Oxidants for Carbene-Catalyzed Radical Reactions

2019 ◽  
Vol 21 (18) ◽  
pp. 7440-7444 ◽  
Author(s):  
Hongling Wang ◽  
Yuhuang Wang ◽  
Xingkuan Chen ◽  
Chengli Mou ◽  
Shuyan Yu ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer

scholarly journals Synthesis of indanes via carbene-catalyzed single-electron-transfer processes and cascade reactions

2017 ◽  
Vol 53 (87) ◽  
pp. 11952-11955 ◽  
Author(s):  
Yuhuang Wang ◽  
Xingxing Wu ◽  
Yonggui Robin Chi
Keyword(s):  
Electron Transfer ◽  
Michael Addition ◽  
Cascade Reactions ◽  
Cascade Reaction ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Transfer Processes ◽  
Electron Transfer Processes

An NHC-catalyzed cascade reaction involving an SET process and two sequential Michael addition steps for the synthesis of indanes is disclosed.

scholarly journals Single electron transfer-based peptide/protein bioconjugations driven by biocompatible energy input

2020 ◽  
Vol 3 (1) ◽  
Author(s):  
Yue Weng ◽  
Chunlan Song ◽  
Chien-Wei Chiang ◽  
Aiwen Lei
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Energy Input ◽  
Limited Range ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Electrochemical Catalysis ◽  
Future Developments ◽  
Recent Developments ◽  
Modified Peptides

AbstractBioconjugation reactions play a central facilitating role in engendering modified peptides and proteins. Early progress in this area was inhibited by challenges such as the limited range of substrates and the relatively poor biocompatibility of bioconjugation reagents. However, the recent developments in visible-light induced photoredox catalysis and electrochemical catalysis reactions have permitted significant novel reactivities to be developed in the field of synthetic and bioconjugation chemistry. This perspective describes recent advances in the use of biocompatible energy input for the modification of peptides and proteins mainly, via the single electron transfer (SET) process, as well as key future developments in this area.

Aromatic substitutions of arenediazonium salts via metal catalysis, single electron transfer, and weak base mediation

2018 ◽  
Vol 16 (27) ◽  
pp. 4942-4953 ◽  
Author(s):  
Denis Koziakov ◽  
Guojiao Wu ◽  
Axel Jacobi von Wangelin
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Weak Base ◽  
Metal Catalysis ◽  
Hazard Potential ◽  
Recent Developments ◽  
Arenediazonium Salts ◽  
Operational Simplicity

Radical aromatic substitutions of arenediazonium salts can be initiated by various methods. The recent developments of weak base-mediated protocols provide great advantages over conventional metal-mediated or photoredox reactions by their operational simplicity, price, hazard potential and scalability.

scholarly journals Aryl radical-mediated N-heterocyclic carbene catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yuki Matsuki ◽  
Nagisa Ohnishi ◽  
Yuki Kakeno ◽  
Shunsuke Takemoto ◽  
Takuya Ishii ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Aryl Iodide ◽  
Alkyl Radicals ◽  
Aryl Radicals ◽  
Electron Transfer Processes ◽  
Secondary Amides

AbstractThere have been significant advancements in radical reactions using organocatalysts in modern organic synthesis. Recently, NHC-catalyzed radical reactions initiated by single electron transfer processes have been actively studied. However, the reported examples have been limited to catalysis mediated by alkyl radicals. In this article, the NHC organocatalysis mediated by aryl radicals has been achieved. The enolate form of the Breslow intermediate derived from an aldehyde and thiazolium-type NHC in the presence of a base undergoes single electron transfer to an aryl iodide, providing an aryl radical. The catalytically generated aryl radical could be exploited as an arylating reagent for radical relay-type arylacylation of styrenes and as a hydrogen atom abstraction reagent for α-amino C(sp3)–H acylation of secondary amides.

scholarly journals Radical reactions promoted by trivalent tertiary phosphines

2020 ◽  
Vol 7 (16) ◽  
pp. 2349-2371 ◽  
Author(s):  
Dingwu Pan ◽  
Guihua Nie ◽  
Shichun Jiang ◽  
Tingting Li ◽  
Zhichao Jin
Keyword(s):  
Electron Transfer ◽  
Single Electron ◽  
Radical Reactions ◽  
Single Electron Transfer ◽  
Tertiary Phosphines

The background and recent breakthroughs in the single-electron-transfer (SET) reactions with trivalent tertiary phosphines are summarized and discussed in detail, and an outlook in the developments within this field is provided.

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