Intramolecular Homolytic Substitution Enabled by Photoredox Catalysis: Sulfur, Phosphorus, and Silicon Heterocycle Synthesis from Aryl Halides

2019 ◽  
Vol 21 (13) ◽  
pp. 5295-5300 ◽  
Author(s):  
Alberto F. Garrido-Castro ◽  
Noelia Salaverri ◽  
M. Carmen Maestro ◽  
José Alemán
Keyword(s):  
Aryl Halides ◽  
Photoredox Catalysis ◽  
Heterocycle Synthesis ◽  
Homolytic Substitution

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

scholarly journals Withdrawal: Photoredox Catalysis Unlocks the Nickel‐Catalyzed Cyanation of Aryl Halides under Benign Conditions

2020 ◽  
Vol 59 (41) ◽  
pp. 17784-17784
Author(s):  
Wen‐Jing Xiao ◽  
Yue Jia ◽  
Yiyin Liu ◽  
Liangqiu Lu ◽  
Hong‐Bin Zhou ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Photoredox Catalysis

scholarly journals Withdrawal: Photoredox Catalysis Unlocks the Nickel‐Catalyzed Cyanation of Aryl Halides under Benign Conditions

2020 ◽  
Vol 132 (41) ◽  
pp. 17935-17935
Author(s):  
Wen‐Jing Xiao ◽  
Yue Jia ◽  
Yiyin Liu ◽  
Liangqiu Lu ◽  
Hong‐Bin Zhou ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Photoredox Catalysis

scholarly journals C–H functionalization of amines with aryl halides by nickel-photoredox catalysis

2016 ◽  
Vol 7 (12) ◽  
pp. 7002-7006 ◽  
Author(s):  
Derek T. Ahneman ◽  
Abigail G. Doyle
Keyword(s):  
Aryl Halides ◽  
Photoredox Catalysis

A redox-neutral method for α-amino C(sp3)–H arylation is described using nickel and photoredox catalysis.

scholarly journals Photoredox Catalysis Unlocks the Nickel-Catalyzed Cyanation of Aryl Halides under Benign Conditions

CCS Chemistry ◽  
2021 ◽  
pp. 1-22
Author(s):  
Yue Jia ◽  
Yi-Yin Liu ◽  
Liang-Qiu Lu ◽  
Shi-Han Liu ◽  
Hong-Bin Zhou ◽  
...  
Keyword(s):  
Aryl Halides ◽  
Photoredox Catalysis

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.

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.

Mild Temperature Copper-Catalyzed Amination of Aryl Halides with Aqueous Ammonia in the Presence of Pyridyldiketone Ligands

2019 ◽  
Author(s):  
Racha Abed Ali Abdine ◽  
Anna Walczak ◽  
Sultan Abu A Aeash ◽  
Gracjan Kurpik ◽  
Artur R. Stefankiewicz ◽  
...  
Keyword(s):  
Catalytic System ◽  
Aqueous Ammonia ◽  
Aryl Halides ◽  
Efficient Coupling ◽  
Ambidentate Ligand ◽  
Mild Temperature

Ambidentate ligand pyridyldiketones were used in combination with copper to catalyze maintain of aryl halides under very mild temperatures. This novel catalytic system allow efficient coupling in one of the smoothest conditions ever reported in literature.

Carbon-Heteroatom Cross-Coupling via an Electronically Excited Nickel (II) Complex

2019 ◽  
Author(s):  
Randolph Escobar ◽  
Jeffrey Johannes
Keyword(s):  
Energy Transfer ◽  
Functional Groups ◽  
Cross Coupling ◽  
Reductive Elimination ◽  
Aryl Halides ◽  
Coupling Reactions ◽  
General Methodology ◽  
Cross Coupling Reactions ◽  
Electronically Excited ◽  
Energy Transfer Pathway

<div>While carbon-heteroatom cross coupling reactions have been extensively studied, many methods are specific and</div><div>limited to a set of substrates or functional groups. Reported here is a method that allows for C-O, C-N and C-S cross coupling reactions under one general methodology. We propose that an energy transfer pathway, in which an iridium photosensitizer produces an excited nickel (II) complex, is responsible for the key reductive elimination step that couples aryl halides to 1° and 2° alcohols, anilines, thiophenols, carbamates and sulfonamides.</div>

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