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Keywords = Koser’s reagent

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11 pages, 1624 KiB  
Communication
Preparation and Synthetic Application of Naproxen-Containing Diaryliodonium Salts
by Jun Zhou, Zhiyuan Bao, Panpan Wu and Chao Chen
Molecules 2021, 26(11), 3240; https://doi.org/10.3390/molecules26113240 - 28 May 2021
Cited by 7 | Viewed by 4071
Abstract
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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14 pages, 104 KiB  
Review
Hypervalent Iodine–Mediated Ring Contraction Reactions
by Luiz F. Silva
Molecules 2006, 11(6), 421-434; https://doi.org/10.3390/11060421 - 20 Jun 2006
Cited by 75 | Viewed by 14268
Abstract
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser ́s [...] Read more.
Hypervalent iodine reagents constitute a powerful tool in modern synthetic organic chemistry, promoting several important reactions. One such reaction is the ring contraction of cycloalkenes and cycloalkanones promoted by iodine(III) compounds, such as iodobenzene diacetate, iodosylbenzene, iodotoluene difluoride, and [hydroxy(tosyloxy)- iodo]benzene (Koser ́s reagent). This review covers all the literature related to the ring contraction of cyclic ketones and olefins promoted by iodine(III) species. Full article
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