Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Pd-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

Опубликована: Ноя. 21, 2023

Diaryliodonium salts are bench stable aryl radical precursors. While photocatalysts generally responsible for generation, recent reports have emerged exhibiting photocatalyst-free generation using select Lewis bases as activators. Herein, we demonstrate 1) the ability of numerous to enable light-driven and 2) these radicals can be captured by transition-metals coupling reactions. These results first step toward developing new organometallic reactions without photocatalysts.

Язык: Английский

Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines DOI
Dmitry I. Bugaenko,

Olga A. Tikhanova,

Valeriy V. Andreychev

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 9923 - 9928

Опубликована: Июль 1, 2024

Diethyl acetamidomalonate (DEAM) has been widely used for the synthesis of α-amino acids via C-alkylation under basic conditions followed by hydrolysis/decarboxylation. In contrast, C-arylation this reagent remains undeveloped. Herein, we report a novel strategy racemic α-arylglycines based on selective arylation DEAM with diaryliodonium salts mild, transition metal-free conditions. The reaction features good functional group tolerance and easy scalability is applicable to chemoselective C-H-modification arenes including approved drugs, thus enabling straightforward approach complex that would be challenging make otherwise.

Язык: Английский

Процитировано

3
Auxiliary strategy for the general and practical synthesis of diaryliodonium(III) salts with diverse organocarboxylate counterions DOI Creative Commons

Naoki Miyamoto,

Daichi Koseki,

Kohei Sumida

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 1020 - 1028

Опубликована: Май 3, 2024

Diaryliodonium(III) salts are versatile reagents that exhibit a range of reactions, both in the presence and absence metal catalysts. In this study, we developed efficient synthetic methods for preparation aryl(TMP)iodonium(III) carboxylates, by reaction (diacetoxyiodo)arenes or iodosoarenes with 1,3,5-trimethoxybenzene diverse organocarboxylic acids. These reactions were conducted under mild conditions using trimethoxyphenyl (TMP) group as an auxiliary, without need additives, excess reagents, counterion exchange further steps. protocols compatible wide substituents on (hetero)aryl iodine(III) compounds, including electron-rich, electron-poor, sterically congested, acid-labile groups, well broad aliphatic aromatic carboxylic acids synthesis carboxylates high yields. This method allows hybridization complex bioactive fluorescent-labeled diaryliodonium(III) salts.

Язык: Английский

Процитировано

2
Overriding Cage Effect in Electron Donor‐Acceptor Photoactivation of Diaryliodonium Reagents: Synthesis of Chalcogenides DOI Open Access

Prahallad Meher,

Sushanta Kumar Parida,

Sanat Kumar Mahapatra

и другие.

Chemistry - A European Journal, Год журнала: 2024, Номер 30(61)

Опубликована: Авг. 26, 2024

In recent times, diaryliodonium reagents (DAIRs) have witnessed a resurgence as arylating reagents, especially under photoinduced conditions. However, reactions proceeding through electron donor-acceptor (EDA) complex formation with DAIRs are restricted to electron-rich reacting partners serving donors due the well-known cage effect. We discovered practical and high-yielding visible-light-induced EDA platform generate aryl radicals from corresponding use them synthesize key chalcogenides. this process, an array of dichalcogenides react in presence 1,4 diazabicyclo[2.2.2]octane (DABCO) cheap readily available donor, furnishing variety di(hetero)aryl aryl/alkyl chalcogenides good yields. The method is scalable, features broad scope yields, operates open-to-air chalcogenation technology suitable for late-stage functionalizations disulfide bioconjugations facilitates access biologically relevant thioesters, dithiocarbamates, sulfoximines, sulfones. Moreover, applies synthesizing diverse pharmaceuticals, such vortioxetine, promazine, mequitazine, dapsone, amenable

Язык: Английский

Процитировано

2
Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts DOI Creative Commons
Ritu Mamgain,

Kokila Sakthivel,

Fateh V. Singh

и другие.

Beilstein Journal of Organic Chemistry, Год журнала: 2024, Номер 20, С. 2891 - 2920

Опубликована: Ноя. 13, 2024

Diaryliodonium salts have become widely recognized as arylating agents in the last two decades. Both, symmetrical and unsymmetrical forms of these serve effective electrophilic reagents various organic syntheses. The use diaryliodoniums C–C carbon–heteroatom bond formations, particularly under metal-free conditions, has further enhanced popularity reagents. In this review, we concentrate on arylation reactions involving carbon other heteroatoms, encompassing rearrangement absence any metal catalyst, summarize advancements made five years.

Язык: Английский

Процитировано

2
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

Опубликована: Март 20, 2024

Herein, we demonstrate 1) that Lewis base heteroatom coordination to diaryliodonium salts is not required for light-driven radical generation and 2) radicals generated by this route can be captured transition-metals coupling reactions. These results are the first step toward developing new aryl reactions without exogenous photocatalysts.

Язык: Английский

Процитировано

1
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI Creative Commons
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

Опубликована: Май 15, 2024

We demonstrate 1) that halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and 2) radi-cals generated by this route can be captured transition-metals C–H arylation reactions. These results are the first step toward devel-oping new metal-catalyzed aryl couplings without exogenous photocatalysts.

Язык: Английский

Процитировано

1
Exogenous Photocatalyst-Free Aryl Radical Generation from Diaryliodonium Salts and use in Metal-Catalyzed C–H Arylation DOI
Jonathan Galicia, Nicholas McDonald,

Christopher Bennett

и другие.

Chemical Communications, Год журнала: 2024, Номер 60(54), С. 6929 - 6932

Опубликована: Янв. 1, 2024

We demonstrate (1) detectable halogen bonding is not critical for enabling light-driven radical generation from diaryliodonium salts and (2) radicals generated by this route can be captured transition-metals C-H arylation reactions. These results are the first step toward developing new metal-catalyzed aryl couplings without exogenous photocatalysts.

Язык: Английский

Процитировано

1
Synthesis of Diaryl Ethers via Hypervalent Iodine-Mediated C–H Functionalization DOI

Chenghu Hu,

Qi Jia,

Wenjing Bao

и другие.

Organic Letters, Год журнала: 2024, Номер 26(37), С. 7864 - 7868

Опубликована: Сен. 9, 2024

A hypervalent iodine-reagent-based C-H functionalization strategy was utilized to synthesize diaryl ethers. This method directly transforms various arenes into their corresponding diaryliodonium salts, followed by a C-O coupling reaction produce structurally diverse The efficacy of this approach in the late-stage structural modifications complex molecules demonstrated.

Язык: Английский

Процитировано

1
One-Pot Photocascade Catalysis: Access to Pyrrole Derivatives from N-Arylglycines and Morita–Baylis–Hillman (MBH) Acetates DOI

Jie Huang,

S.-L. You,

Ling-Zhi Hu

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 18, 2024

The step-economical synthesis of pyrrole derivatives has posed a challenge in the field

Язык: Английский

Процитировано

1
Visible Light-Promoted and Catalyst-Controlled α-Aminoalkylation and α-Diaminoalkylation of Morita-Baylis–Hillman Acetates with N-Methyl Arylamines: Divergent Synthesis of N-Containing Alkyl Acrylates and γ,γ-Diaminobutyl Esters DOI
Xiao‐Hong Huang,

Xiao Hu,

Ting-Feng Fu

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Дек. 2, 2024

Visible light-promoted α-aminoalkyl radical-triggered α-aminoalkylation and α-diaminoalkylation of Morita-Baylis–Hillman acetates with N-methyl arylamines to synthesize N-containing alkyl acrylates γ,γ-diaminobutyl esters was reported. Photoinduced is carried out Na2-eosin Y as an organophotocatalyst at room temperature under metal- oxidant-free conditions. In particular, the performed via radical addition/elimination followed by a catalyst-controlled selective addition strategy in one step [Ir(dtbbpy)(bpy)2)]PF6/KF catalytic system. The reaction highly atom- step-economic, high selectivity, furnishing butyl moderate good yields wide substrate scope.

Язык: Английский

Процитировано

1