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 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 Alcohol-Initiated Dediazoniation of Aryldiazonium Ions to Aryl Radicals: A Simple and Efficient Route to Arylboronates

2018 ◽  
Vol 42 (9) ◽  
pp. 481-485
Author(s):  
Xiulian Zhang ◽  
Zhicheng Zhang ◽  
Yongbin Xie ◽  
Yujie Jiang ◽  
Ruibo Xu ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Bond Formation ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Aryl Radical ◽  
Radical Species ◽  
Aryl Radicals ◽  
Efficient Access ◽  
Efficient Route ◽  
Operational Simplicity

A simple and efficient access to arylboronates was achieved with methanol-initiated borylation of aryldiazonium salts. Reduction of aryldiazonium ions by single electron transfer from methanol affords aryl radical species, which undergo a subsequent C–B bond formation with bis(pinacolato)diboron. This highly practical borylation process, which can be carried out on the gram-scale, enjoys operational simplicity as well as mild and catalyst-free conditions.

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.

Weak Base-Promoted Selective Rearrangement of Oxaziridines to Amides via Visible-Light Photoredox Catalysis

2021 ◽  
Author(s):  
Jin Park ◽  
Sehoon Park ◽  
Gwang Seok Jang ◽  
Ran Hui Kim ◽  
Jaehoon Jung ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Photoredox Catalysis ◽  
Weak Base

The selective rearrangement of oxaziridines to amides via single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amides via...

Single electron transfer-induced coupling of alkynylzinc reagents with aryl and alkenyl iodides

2016 ◽  
Vol 52 (97) ◽  
pp. 14019-14022 ◽  
Author(s):  
Keisho Okura ◽  
Hitomi Kawashima ◽  
Fumiko Tamakuni ◽  
Naoya Nishida ◽  
Eiji Shirakawa
Keyword(s):  
Electron Transfer ◽  
Transition Metal ◽  
Transition Metal Catalysis ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Metal Catalysis ◽  
First Time

An alkynyl–aryl coupling without the aid of transition metal catalysis has been achieved for the first time.

Reversal of Polarity by Catalytic SET Oxidation: Synthesis of Azabicyclo[m.n.o]alkanes via Chemoselective Reduction of Amidines

2021 ◽  
Author(s):  
Sundarababu Baskaran ◽  
Kirana D V ◽  
Kanak Kanti Das
Keyword(s):  
Electron Transfer ◽  
Stereoselective Synthesis ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Catalytic Method ◽  
One Pot ◽  
Oxidative System ◽  
Oxidation Synthesis

A one-pot catalytic method has been developed for the stereoselective synthesis of cyclopropane-fused cyclic amidines using CuBr2/K2S2O8 as an efficient single electron transfer (SET) oxidative system. The generality of this...

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