The Preparation and Application of Diaryliodonium Salts Derived from Gemfibrozil and Gemfibrozil Methyl Ester

Synthesis ◽  
2021 ◽  
Author(s):  
Jun Zhou ◽  
Zhiyuan Bao ◽  
Panpan Wu ◽  
Chao Chen
Keyword(s):  
Methyl Ester ◽  
Iodonium Salts ◽  
Diaryliodonium Salts

The diaryliodonium salts derived from gemfibrozil and gemfibrozil methyl ester have been synthesized with ArI(OH)OTs or bis(4-methoxyphenyl) iodonium diacetate with good regio-selectivity. Those iodonium salts have been successfully used in derivatization of gemfibrozil or gemfibrozil methyl ester, including fluorination, alkynylation and arylation, etherification, esterification and iodination reactions.

scholarly journals Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3240
Author(s):  
Jun Zhou ◽  
Zhiyuan Bao ◽  
Panpan Wu ◽  
Chao Chen
Keyword(s):  
Methyl Ester ◽  
Aromatic Ring ◽  
Solvent Mixture ◽  
Iodonium Salts ◽  
Diaryliodonium Salts ◽  
Esterification Reactions ◽  
Trimethylsilyl Trifluoromethanesulfonate ◽  
Synthetic Application ◽  
Hydrolysis Of ◽  
Naproxen Methyl Ester

The synthesis of naproxen-containing diaryliodonium salts has been realized from naproxen methyl ester and ArI(OH)OTs activated by trimethylsilyl trifluoromethanesulfonate (TMSOTf) in a solvent mixture comprising dichloromethane and 2,2,2-trifluoroethanol (TFE). Those iodonium salts have been successfully used in the functionalization of an aromatic ring of naproxen methyl ester, including fluorination, iodination, alkynylation, arylation, thiophenolation, and amination and esterification reactions. Moreover, further hydrolysis of the obtained 5-iodo-naproxen methyl ester afforded 5-iodo-naproxen.

One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

2020 ◽  
Author(s):  
Lucien Caspers ◽  
Julian Spils ◽  
Mattis Damrath ◽  
Enno Lork ◽  
Boris Nachtsheim
Keyword(s):  
Conformational Analysis ◽  
Bronsted Acids ◽  
One Pot ◽  
Benzyl Alcohols ◽  
Iodonium Salts ◽  
Efficient Approach ◽  
One Pot Synthesis ◽  
Diaryliodonium Salts

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

scholarly journals Synthesis of fluoro-functionalized diaryl-λ3-iodonium salts and their cytotoxicity against human lymphoma U937 cells

2018 ◽  
Vol 14 ◽  
pp. 364-372 ◽  
Author(s):  
Prajwalita Das ◽  
Etsuko Tokunaga ◽  
Hidehiko Akiyama ◽  
Hiroki Doi ◽  
Norimichi Saito ◽  
...  
Keyword(s):  
Biological Properties ◽  
U937 Cells ◽  
Iodonium Salts ◽  
Diaryliodonium Salts ◽  
Sterically Demanding ◽  
Diaryliodonium Salt ◽  
Human Lymphoma ◽  
Normal Human ◽  
Human B Cell

Conscious of the potential bioactivity of fluorine, an investigation was conducted using various fluorine-containing diaryliodonium salts in order to study and compare their biological activity against human lymphoma U937 cells. Most of the compounds tested are well-known reagents for fluoro-functionalized arylation reactions in synthetic organic chemistry, but their biological properties are not fully understood. Herein, after initially investigating 18 fluoro-functionalized reagents, we discovered that the ortho-fluoro-functionalized diaryliodonium salt reagents showed remarkable cytotoxicity in vitro. These results led us to synthesize more compounds, previously unknown sterically demanding diaryliodonium salts having a pentafluorosulfanyl (SF5) functional group at the ortho-position, that is, unsymmetrical ortho-SF5 phenylaryl-λ3-iodonium salts. Newly synthesized mesityl(2-(pentafluoro-λ6-sulfanyl)phenyl)iodonium exhibited the greatest potency in vitro against U937 cells. Evaluation of the cytotoxicity of selected phenylaryl-λ3-iodonium salts against AGLCL (a normal human B cell line) was also examined.

Transition metal-free N-arylation of secondary amides through iodonium salts as aryne precursors

2016 ◽  
Vol 14 (43) ◽  
pp. 10185-10188 ◽  
Author(s):  
Ming Wang ◽  
Zhijian Huang
Keyword(s):  
Transition Metal ◽  
Iodonium Salts ◽  
Metal Free ◽  
Diaryliodonium Salts ◽  
Secondary Amides

A transition metal-free approach for N-arylation of secondary amides was developed via diaryliodonium salts as aryne precursors.

scholarly journals One-Pot Synthesis and Conformational Analysis of 6-Membered Cyclic Iodonium Salts

2020 ◽  
Author(s):  
Lucien Caspers ◽  
Julian Spils ◽  
Mattis Damrath ◽  
Enno Lork ◽  
Boris Nachtsheim
Keyword(s):  
Conformational Analysis ◽  
Bronsted Acids ◽  
One Pot ◽  
Benzyl Alcohols ◽  
Iodonium Salts ◽  
Efficient Approach ◽  
One Pot Synthesis ◽  
Diaryliodonium Salts

In this article we describe an efficient approach for the synthesis of cyclic diaryliodonium salts. The method is based on benzyl alcohols as starting materials and consists of an Friedel-Crafts-arylation/oxidation sequence. Besides a deep optimization, particluar focusing on the choice and ratios of the utilized Bronsted-acids and oxidants, we explore the substrate scope of this transformation. We also discuss an interesting isomerism of cyclic iodonium salts substituted with aliphatic substituents at the bridge head carbon. <br>

scholarly journals Palladium-catalyzed synthesis of N-arylated carbazoles using anilines and cyclic diaryliodonium salts

2013 ◽  
Vol 9 ◽  
pp. 1202-1209 ◽  
Author(s):  
Stefan Riedmüller ◽  
Boris J Nachtsheim
Keyword(s):  
Direct Synthesis ◽  
Iodonium Salts ◽  
Aniline Derivatives ◽  
Diaryliodonium Salts ◽  
Palladium Catalyzed

The direct synthesis of N-arylated carbazoles through a palladium-catalyzed amination of cyclic iodonium salts with anilines is described. In particular, electron-poor aniline derivatives reacted smoothly with only 5 mol % of Pd(OAc)2 as catalyst to give the desired products in up to 71% yield. Furthermore, the reactivity of cyclic iodonium salts is compared with the reactivity of the corresponding cyclic bromonium analogues.

scholarly journals One-pot synthesis of diaryliodonium salts from arenes and aryl iodides with Oxone–sulfuric acid

2018 ◽  
Vol 14 ◽  
pp. 849-855 ◽  
Author(s):  
Natalia Soldatova ◽  
Pavel Postnikov ◽  
Olga Kukurina ◽  
Viktor V Zhdankin ◽  
Akira Yoshimura ◽  
...  
Keyword(s):  
Sulfuric Acid ◽  
Facile Synthesis ◽  
One Pot ◽  
Iodonium Salts ◽  
Wide Applicability ◽  
One Pot Synthesis ◽  
Diaryliodonium Salts ◽  
Aryl Iodides

A facile synthesis of diaryliodonium salts utilizing Oxone as versatile and cheap oxidant has been developed. This method shows wide applicability and can be used for the preparation of iodonium salts containing electron-donating or electron-withdrawing groups in good yields. In addition, this procedure can be applied to the preparation of symmetric iodonium salts directly from arenes via a one-pot iodination–oxidation sequence.

The Effect of Some Synthetic Arginyl and Lysyl Compounds on Clotting and Fibrinolysis

1972 ◽  
Vol 28 (02) ◽  
pp. 289-298 ◽  
Author(s):  
M. J Weinstein ◽  
R. F Doolittle
Keyword(s):  
Methyl Ester ◽  
Thrombin Activation

SummaryThe effects of a number of synthetic arginyl- and lysyl-compounds on clotting and fibrinolysis have been studied. The lysyl derivatives had no significant effect on the clotting of recalcified plasma or recalcified euglobulin preparations, but tosyllysine (TL) and tosyllysine methyl ester (TLME) were very effective inhibitors of fibrinolysis. Certain arginyl-peptides (in particular, tosylarginylsarcosine methyl ester) were very effective at delaying clotting in these systems. These same substances gave rise to an exaggerated thrombin production, however, evidently by interfering with the natural thrombin activation of plasma antithrombin(s).

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