Visible light mediated synthesis of 4-aryl-1,2-dihydronaphthalene derivatives via single-electron oxidation or MHAT from methylenecyclopropanes

2021 ◽  
Vol 8 (1) ◽  
pp. 94-100
Author(s):  
Jiaxin Liu ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Visible Light ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Synthetic Strategy ◽  
Rapid Construction

A new synthetic strategy of a single-electron oxidation and MHAT of methylenecyclopropanes (MCPs) for the rapid construction of 4-aryl-1,2-dihydronaphthalene derivatives by merging photoredox catalysis and cobalt catalysis has been developed.

scholarly journals α-Functionalization of Imines via Visible Light Photoredox Catalysis

Catalysts ◽  
2020 ◽  
Vol 10 (5) ◽  
pp. 562 ◽  
Author(s):  
Alberto F. Garrido-Castro ◽  
M. Carmen Maestro ◽  
José Alemán
Keyword(s):  
Visible Light ◽  
Building Blocks ◽  
Single Electron ◽  
Synthetic Chemistry ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Radical Intermediates ◽  
Research Programs ◽  
Electron Reduction

The innate electrophilicity of imine building blocks has been exploited in organic synthetic chemistry for decades. Inspired by the resurgence in photocatalysis, imine reactivity has now been redesigned through the generation of unconventional and versatile radical intermediates under mild reaction conditions. While novel photocatalytic approaches have broadened the range and applicability of conventional radical additions to imine acceptors, the possibility to use these imines as latent nucleophiles via single-electron reduction has also been uncovered. Thus, multiple research programs have converged on this issue, delivering creative and practical strategies to achieve racemic and asymmetric α-functionalizations of imines under visible light photoredox catalysis.

A Single Electron Transfer (SET) Approach to C–H Amidation of Hydrazones via Visible-Light Photoredox Catalysis

2016 ◽  
Vol 18 (20) ◽  
pp. 5356-5359 ◽  
Author(s):  
Muliang Zhang ◽  
Yingqian Duan ◽  
Weipeng Li ◽  
Pan Xu ◽  
Jian Cheng ◽  
...  
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Single Electron ◽  
Single Electron Transfer ◽  
Photoredox Catalysis

scholarly journals A Multiphoton Single-Electron Reduction of Olefins via Tandem Photoredox Catalysis

2020 ◽  
Author(s):  
Tyra Horngren ◽  
Mitchell S. Taylor ◽  
Milena Czyz ◽  
Anastasios Polyzos
Keyword(s):  
Visible Light ◽  
Radical Anion ◽  
Hydrogen Gas ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Electron Reduction

<p><a></a>Herein we report a visible light multiphoton tandem photoredox catalysis strategy enabling a distinctive mode of olefin activation via a one electron reduction to the corresponding radical anion. This highly nucleophilic intermediate was harnessed to develop a method for the formal hydrogenation of unactivated alkenes under mild reaction conditions, in the absence of hydrogen gas or dissolving metals. <b></b></p>

Bromine Cation Initiated vic-Diphosphination of Styrenes with Diphosphines under Photoredox Catalysis

Synthesis ◽  
2018 ◽  
Vol 50 (17) ◽  
pp. 3402-3407 ◽  
Author(s):  
Koji Hirano ◽  
Masahiro Miura ◽  
Nobutaka Otomura ◽  
Yuto Okugawa
Keyword(s):  
Visible Light ◽  
Functional Group ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Reaction Efficiency ◽  
Key Species ◽  
Electron Reduction

An N-bromosuccinimide (NBS)-initiated vic-diphosphination of styrenes with diphosphines proceeds under visible-light-promoted Ir(ppy)3 photoredox catalysis to deliver the corresponding 1,2-diphosphinoethane derivatives in good yields. The NBS is a bromine cation source and generates a bromophosphine, which undergoes a single-electron reduction by the excited iridium species to form phosphinyl radicals of key species in the diphoshination reaction. The newly developed photoredox catalysis demonstrates better reaction efficiency, functional group compatibility, and scalability than the previous photocatalysis using N-fluorobenzenesulfonimide (NFSI) and silylphosphine.

scholarly journals Visible-Light-Mediated Photocatalytic Oxidative C–C Bond Cleavage of Geminal Diazides: An Approach to Oxamates

SynOpen ◽  
2021 ◽  
Vol 05 (02) ◽  
pp. 152-157
Author(s):  
Duddu S. Sharada ◽  
Narenderreddy Katta ◽  
Arumugavel Murugan ◽  
Sonika Sharma
Keyword(s):  
Electron Transfer ◽  
Visible Light ◽  
Bond Cleavage ◽  
Organic Dye ◽  
Single Electron ◽  
Mechanistic Study ◽  
Single Electron Transfer ◽  
Photoredox Catalysis ◽  
The Past ◽  
Remarkable Progress

AbstractPhotoredox catalysis has received great attention in both academia and industry and remarkable progress has been made over the past decade. Now, it has been shown that a visible-light-mediated oxidative C–C bond cleavage of geminal diazides can be induced by organic dye catalysis for the synthesis of oxamates. A mechanistic study, confirmed by control experiments, indicates that this proceeds through single-electron transfer (SET). This methodology can be applied to convert a wide array of geminal diazides into oxamates.

A Multiphoton Single-Electron Reduction of Olefins via Tandem Photoredox Catalysis

2020 ◽  
Author(s):  
Tyra Horngren ◽  
Mitchell S. Taylor ◽  
Milena Czyz ◽  
Anastasios Polyzos
Keyword(s):  
Visible Light ◽  
Radical Anion ◽  
Hydrogen Gas ◽  
Single Electron ◽  
Photoredox Catalysis ◽  
Reaction Conditions ◽  
Electron Reduction

<p><a></a>Herein we report a visible light multiphoton tandem photoredox catalysis strategy enabling a distinctive mode of olefin activation via a one electron reduction to the corresponding radical anion. This highly nucleophilic intermediate was harnessed to develop a method for the formal hydrogenation of unactivated alkenes under mild reaction conditions, in the absence of hydrogen gas or dissolving metals. <b></b></p>

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...

Arylsulfonylacetamides as bifunctional reagents for alkene aminoarylation

Science ◽  
2018 ◽  
Vol 361 (6409) ◽  
pp. 1369-1373 ◽  
Author(s):  
Timothy M. Monos ◽  
Rory C. McAtee ◽  
Corey R. J. Stephenson
Keyword(s):  
Sulfur Dioxide ◽  
Visible Light ◽  
Room Temperature ◽  
Functional Group ◽  
Bond Formation ◽  
Single Electron ◽  
Convergent Synthesis ◽  
Alkene Oxidation ◽  
Synthetic Strategy ◽  
Nitrogen Bond

Alkene aminoarylation with a single, bifunctional reagent is a concise synthetic strategy. We report a catalytic protocol for the addition of arylsulfonylacetamides across electron-rich alkenes with complete anti-Markovnikov regioselectivity and excellent diastereoselectivity to provide 2,2-diarylethylamines. In this process, single-electron alkene oxidation enables carbon-nitrogen bond formation to provide a key benzylic radical poised for a Smiles-Truce 1,5-aryl shift. This reaction is redox-neutral, exhibits broad functional group compatibility, and occurs at room temperature with loss of sulfur dioxide. As this process is driven by visible light, uses readily available starting materials, and demonstrates convergent synthesis, it is well suited for use in a variety of synthetic endeavors.

Generation of Phosphoranyl Radicals via Photoredox Catalysis Enables Voltage–Independent Activation of Strong C–O Bonds

2018 ◽  
Author(s):  
Erin Stache ◽  
Alyssa B. Ertel ◽  
Tomislav Rovis ◽  
Abigail G. Doyle
Keyword(s):  
Carboxylic Acids ◽  
Functional Groups ◽  
Single Step ◽  
Direct Access ◽  
Photoredox Catalysis ◽  
Acyl Radical ◽  
Synthetic Strategy ◽  
Acyl Radicals ◽  
Benzyl Radicals ◽  
Aliphatic Carboxylic Acids

Alcohols and carboxylic acids are ubiquitous functional groups found in organic molecules that could serve as radical precursors, but C–O bonds remain difficult to activate. We report a synthetic strategy for direct access to both alkyl and acyl radicals from these ubiquitous functional groups via photoredox catalysis. This method exploits the unique reactivity of phosphoranyl radicals, generated from a polar/SET crossover between a phosphine radical cation and an oxygen centered nucleophile. We first show the desired reactivity in the reduction of benzylic alcohols to the corresponding benzyl radicals with terminal H-atom trapping to afford the deoxygenated product. Using the same method, we demonstrate access to synthetically versatile acyl radicals which enables the reduction of aromatic and aliphatic carboxylic acids to the corresponding aldehydes with exceptional chemoselectivity. This protocol also transforms carboxylic acids to heterocycles and cyclic ketones via intramolecular acyl radical cyclizations to forge new C–O, C–N and C–C bonds in a single step.

Regioselective C3-H Trifluoromethylation of 2H-Indazole Under Transition-Metal-Free Photoredox Catalysis

2019 ◽  
Author(s):  
Arumugavel Murugan ◽  
Venkata Nagarjuna Babu ◽  
Nagaraj Sabarinathan ◽  
Sharada Duddu. S
Keyword(s):  
Transition Metal ◽  
Visible Light ◽  
Practical Approach ◽  
Hypervalent Iodine ◽  
Radical Mechanism ◽  
Photoredox Catalysis ◽  
Metal Free

Here we report a visible-light-promoted metal-free regioselective C3-H trifluoromehtylation reaction that proceeds via radical mechanism and which supported by control experiments. The combination of photoredox catalysis and hypervalent iodine reagent provides a practical approach for the present trifluoromethylation reaction and synthesis of a library of trifluoromethylated indazoles.

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