Photoredox catalyzed cascade CF3 addition/chemodivergent annulations of ortho-alkenyl aryl ureas

2022 ◽  
Author(s):  
Sakamuri Sarath Babu ◽  
A Anagha Varma ◽  
Purushothaman Gopinath
Keyword(s):  
Photoredox Catalysis ◽  
Cascade Cyclization ◽  
Ambident Nucleophile

Herein, we report a substrate-controlled cascade cyclization of o-alkenyl aryl ureas, an ambident nucleophile for constructing functionalized heterocycles such as 2-amino-1,3-benzoxazines and dihydroquinazolinones in a chemodivergent fashion using photoredox catalysis...

Synthesis of trifluoroalkyl or difluoroalkyl phenanthridine derivatives via cascade reaction using an intramolecular cyano group as a radical acceptor under photoredox catalysis

2018 ◽  
Vol 16 (3) ◽  
pp. 414-423 ◽  
Author(s):  
Xu Liu ◽  
Zhongjie Wu ◽  
Zeguo Zhang ◽  
Ping Liu ◽  
Peipei Sun
Keyword(s):  
Visible Light ◽  
Visible Light Irradiation ◽  
Cyano Group ◽  
Cascade Reaction ◽  
Light Irradiation ◽  
Photoredox Catalysis ◽  
Cascade Cyclization ◽  
Radical Acceptor ◽  
Cyclization Process

In the presence of Ru(phen)3Cl2 or fac-Ir(ppy)3 under visible-light irradiation, the addition of fluorinated radicals to N-arylacrylamides followed by an intramolecular cyano group insertion cascade cyclization process produced the target compounds in moderate to good yields.

Cascade cyclization of glycine derivatives with β-ketoesters for polysubstituted 1,4-dihydropyridines by visible light photoredox catalysis

Tetrahedron ◽  
2020 ◽  
Vol 76 (33) ◽  
pp. 131353
Author(s):  
Xiao Zhu ◽  
Zhi-Qiang Zhu ◽  
Dong Guo ◽  
Shan Liu ◽  
Jiu-Jian Ji ◽  
...  
Keyword(s):  
Visible Light ◽  
Photoredox Catalysis ◽  
Cascade Cyclization ◽  
Glycine Derivatives

scholarly journals Cascade cyclization reactions of alkylidenecyclopropanes for the construction of polycyclic lactams and lactones by visible light photoredox catalysis

2020 ◽  
Vol 7 (2) ◽  
pp. 374-379 ◽  
Author(s):  
Mintao Chen ◽  
Yin Wei ◽  
Min Shi
Keyword(s):  
Visible Light ◽  
Membered Ring ◽  
Visible Light Photocatalysis ◽  
Photoredox Catalysis ◽  
Cyclization Reactions ◽  
Cascade Cyclization

A facile method for the synthesis of seven- and eight-membered ring-containing polycyclic lactams and lactones by visible light photocatalysis has been developed.

Spin-Forbidden Excitation Enables Infrared Photoredox Catalysis

2020 ◽  
Author(s):  
Tomislav Rovis ◽  
Benjamin D. Ravetz ◽  
Nicholas E. S. Tay ◽  
Candice Joe ◽  
Melda Sezen-Edmonds ◽  
...  
Keyword(s):  
Excited State ◽  
Ground State ◽  
Intersystem Crossing ◽  
Photoredox Catalysis ◽  
Infrared Irradiation ◽  
Triplet Excitation ◽  
New Family ◽  
Ir Light

We describe a new family of catalysts that undergo direct ground state singlet to excited state triplet excitation with IR light, leading to photoredox catalysis without the energy waste associated with intersystem crossing. The finding allows a mole scale reaction in batch using infrared irradiation.

Fe-Catalyzed Conjunctive Cross-Couplings of Unactivated Alkenes with Grignard Reagents

2020 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Cassandra R. Youshaw ◽  
Mingbin Yuan ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Functional Groups ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Turnover Frequency ◽  
Diverse Range ◽  
Cascade Cyclization ◽  
Radical Cascade

The first iron-catalyzed three-component cross-coupling of unactivated olefins with alkyl halides and Grignard reagents is reported. The reaction operates under fast turnover frequency and tolerates a diverse range of sp2-hybridized nucleophiles, alkyl halides, and unactivated olefins bearing diverse functional groups to yield the desired 1,2-alkylarylated products with high regiocontrol. Further, we demonstrate that this protocol is amenable for the synthesis of new (hetero)carbocycles including tetrahydrofurans and pyrrolidines via a three-component radical cascade cyclization/arylation that forges three new C-C bonds.

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.

scholarly journals Tandem photoelectrochemical and photoredox catalysis for efficient and selective aryl halides functionalization by solar energy

Matter ◽  
2021 ◽  
Author(s):  
Ya-Jing Chen ◽  
Tao Lei ◽  
Hui-Lan Hu ◽  
Hao-Lin Wu ◽  
Shuai Zhou ◽  
...  
Keyword(s):  
Solar Energy ◽  
Aryl Halides ◽  
Photoredox Catalysis
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