iodonium salts
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2022 ◽  
Author(s):  
Shubhendu Karandikar ◽  
David Ross Stuart
Keyword(s):  

Aryl(Mes)iodonium salts, which are multifaceted aryl transfer reagents, are synthesized via boron-iodane exchange. Modification to both the nucleophilic (aryl boron) and electrophilic (mesityl-λ3-iodane) reaction components result in improved yield and...


2022 ◽  
Author(s):  
Yaxing Wu ◽  
Chao Wu ◽  
Fei Wang ◽  
Chao Chen

A [2+2+1] annulation protocol has been established for the modular synthesis of 2,4-disubstituted thiophenes/selenophens, with excellent regioselectivity. The reactions are catalyzed by copper salt with elemental sulfur and selenium serving...


Synthesis ◽  
2021 ◽  
Author(s):  
Jun Zhou ◽  
Zhiyuan Bao ◽  
Panpan Wu ◽  
Chao Chen

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.


2021 ◽  
Author(s):  
Andreas Boelke ◽  
Soleicha Sadat ◽  
Enno Lork ◽  
Boris Nachtsheim

In this manuscript we describe novel bicationic iodonium salts which are stabilized by covalently connected <i>N</i>-heterocycles (Bis-<i>N</i>-Heterocycle-stabilized Iodanes BNHIs). We provide structural data, their synthesis as well as their application in benchmark oxidative transformations.


2021 ◽  
Author(s):  
Andreas Boelke ◽  
Soleicha Sadat ◽  
Enno Lork ◽  
Boris Nachtsheim

In this manuscript we describe novel bicationic iodonium salts which are stabilized by covalently connected <i>N</i>-heterocycles (Bis-<i>N</i>-Heterocycle-stabilized Iodanes BNHIs). We provide structural data, their synthesis as well as their application in benchmark oxidative transformations.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3240
Author(s):  
Jun Zhou ◽  
Zhiyuan Bao ◽  
Panpan Wu ◽  
Chao Chen

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.


Synthesis ◽  
2021 ◽  
Author(s):  
Zhan-Yong Wang ◽  
Qi Guo ◽  
Shaohong Xu ◽  
Kai-Kai Wang

P(O)-H compounds like H-phosphites, H-phosphinates and H-phosphine oxides are widely used as nucleophiles. Herein, reactions with unsaturated compounds, C-H activation, Hiro reaction, P-C, P-S, P-O, P-N and P-F couplings were thoroughly discussed and summarized. This review will focus on their reactions with alkenes, alkynes, enamides, propiolic acids, epoxide, arynes, arenes, quinones, isothiocyanates, diazo compounds, aldehydes, ketones, imines, pyridines, acid derivatives, carbocations, aryl halides, dibromoalkenes, disulfides, thiosulfates, sulfonyl chlorides, iodonium salts, amines, alcohols and thioalcohols.


Author(s):  
V. Zhdankin

This review summarizes industrial applications of inorganic and organic polyvalent (hypervalent) iodine compounds. Inorganic iodate salts have found some application as a dietary supplements and food additives. Iodine pentafluoride is used as industrial fluorinating reagent, and iodine pentoxide is a powerful and selective oxidant that is particularly useful in analytical chemistry. Common organic hypervalent iodine reagents such as (dichloroiodo)benzene and (diacetoxyiodo)benzene are occasionally used in chemical industry as the reagents for production of important pharmaceutical intermediates. Iodonium salts have found industrial application as photoinitiators for cationic photopolymerizations. Various iodonium compounds are widely used as precursors to [18F]-fluorinated radiotracers in the Positron Emission Tomography (PET).


2021 ◽  
Author(s):  
Andreas Boelke ◽  
Thomas Kuczmera ◽  
Enno Lork ◽  
Boris Nachtsheim

Herein we describe the first systematic investigation of cyclic iodonium salts (iodoliums and iodazoliums) and their performance as XB-donors in a variety of benchmark reactions. It was found that further <i>N</i>-alklyation of the <i>N</i>-heterocycle has a significant influence on their XB-donor capability. These novel dicationic species show a reactivity which is comparable or even better than the best so far described iodine(I) and iodine(III) compounds throughout the investigated reaction set. <br>


2021 ◽  
Author(s):  
Andreas Boelke ◽  
Thomas Kuczmera ◽  
Enno Lork ◽  
Boris Nachtsheim

Herein we describe the first systematic investigation of cyclic iodonium salts (iodoliums and iodazoliums) and their performance as XB-donors in a variety of benchmark reactions. It was found that further <i>N</i>-alklyation of the <i>N</i>-heterocycle has a significant influence on their XB-donor capability. These novel dicationic species show a reactivity which is comparable or even better than the best so far described iodine(I) and iodine(III) compounds throughout the investigated reaction set. <br>


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