Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents

Yadav, J. S.; Reddy, B. V. Subba; Basak, A. K.; Narsaiah, A. Venkat

doi:10.1016/j.tet.2003.12.056

Cited by 85 publications

(36 citation statements)

References 37 publications

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“…The third approach, a Suzuki coupling to (7E,9Z)-octadecadienoic acid (C) (Scheme 4), started with 1-decyne (17) and 7-octyn-1-ol (21), prepared from 2-octyne-1-ol (20) through Zipper reaction (17). To obtain the boronic acid (22), 7-octyne-1-ol was reacted with 1,3,2-benzodioxaborole using THF as the solvent.…”

Section: Resultsmentioning

confidence: 99%

“…Oxidation with pyridinium dichromate yielded the desired products in yields up to 45%, and lower amounts of by-products were formed. A third method proved to be even superior to PDC: During a two-step procedure, the alcohol is first oxidized to the aldehyde [e.g., Swern oxidation (19) or Dess-Martin oxidation (20)], which is then further oxidized with sodium chlorite (21). Although the synthesis of CLA involves an additional step, yields were higher and purification of the crude products was easier.…”

Section: Resultsmentioning

confidence: 99%

“…The resulting yellow solution was stirred for an additional 20 min. The mixture was cooled in a water bath, and 4.5 g (36 mmol) 2-octyne-1-ol (20) was slowly added so that the temperature remained below 30°C. After stirring for 30 min at room temperature, the solution was poured into ice water and extracted four times with hexane.…”

Section: Methodsmentioning

confidence: 99%

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Syntheses of conjugated octadecadienoic acids

Kellersmann¹,

Steinhart²,

Francke³

2006

Lipids

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Syntheses of conjugated octadecadienoic acids

Kellersmann¹,

Steinhart²,

Francke³

2006

Lipids

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“…Ionic liquids offer interesting and useful features that are advantageous to organic reactions such as negligible vapor pressure, nonflammability, high thermal stability, and easy reusability. In this regard, ionic liquids have been successfully used in the Friedel-Crafts reaction [31][32][33], hydrogenation [34][35][36], Diels-Alder reactions [37][38][39], Mizoroki-Heck, Suzuki-Miyaura, Sonogashira, and olefin metathesis reactions [40][41][42][43][44], Michael additions [45], oxidation [46][47][48][49][50][51][52][53][54], condensation reaction [55][56][57][58][59], formation of imines [60], 1,2-rearrangement [61], esterification of carboxylic acids and carboxylates [62][63][64][65], Williamson ether synthesis [66][67][68][69][70][71][72], and the Grignard reaction [73,74]. We have reported efficient methods for the esterification of carboxylic acids and phosphonic acids with trialkyl orthoacetate in ionic liquid <...>…”

Section: Introductionmentioning

confidence: 99%

Preparation of α-Bromoketones and Thiazoles from Ketones with NBS and Thioamides in Ionic Liquids

Izumisawa¹,

Togo²

2011

GSC

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Ketones smoothly reacted with NBS in the presence of a catalytic amount of p-toluenesulfonic acid to give α-bromoketones in good yields in typical ionic liquids, such as [bmim]PF 6 and [bmpy]Tf 2 N, and the ionic liquids could be repeatedly used for the same reaction after the extraction of the α-bromoketones. Then, the one-pot conversion of ketones into thiazoles by the treatment with NBS, and subsequently with thioamides could be also carried out in [bmim]PF 6 and [bmpy]Tf 2 N, respectively Thus, [bmim]PF 6 and [bmpy]Tf 2 N could be used as recyclable reaction media for the preparation α-bromoketones and thiazoles from ketones.

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“…Hypervalent iodine reagent in ionic liquids reportedly leads to mild chemoselective and in some cases regioselective oxidative transformations. 20 Our laboratory had previously used ionic liquids in synthetic carbohydrate chemistry. 21 Compound 10 was dissolved in 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim] + BF4 − ) and treated with 1.5 equiv of Dess-Martin periodinane for 3 h to afford the corresponding aldehyde 11.…”

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confidence: 99%

Synthesis of Double C-Glycoside Analogue of sTn

et al. 2005

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A sTn double C-glycoside, sTn analogue 2, was synthesized using samarium chemistry developed in our laboratory. Complications in the oxidation reaction affording aldehyde acceptor were overcome by double protection of amide and the use of a room-temperature ionic liquid as solvent. Studies are underway to conjugate the sTn double C-glycoside hapten 2 to KLH carrier protein for biological evaluation as a vaccine.Neuraminic acids are biologically important since they occupy the terminal position of the glycans on macro-molecules outside cells and cell membranes and are involved in recognition, cell interactions, neuronal transmission, ion transport, reproduction, differentiation, epitope masking, and protection. Neuraminic acids are also involved in pathological processes including infection, inflammations, cancer, and neurological, cardiovascular, endocrinological, and autoimmune diseases. 1,2 Cell surfaces containing these terminal neuraminic acids interact with receptors, hormones, enzymes, toxins, and viruses and other pathogens that use Neu5Ac to localize on the surface of cells they infect. 3 The linkage of neuraminic acid to glycoconjugates is among the most labile glycosidic linkages and is cleaved in vitro under mildly acidic conditions. In vivo, neuraminic acidcontaining glycoconjugates are catabolized through the removal of the terminal sialic acid residue by the action of hydrolase-type enzymes called neuraminidases. A non-hydrolyzable glycosidic linkage to neuraminic acid represents is an attractive approach to design reagents for glycobiology and immunology. The replacement of the interglycosidic oxygen atom with a hydroxymethylene group using SmI 2 chemistry 4 affords a class of hydrolytically and

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Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents

Cited by 85 publications

References 37 publications

Syntheses of conjugated octadecadienoic acids

Syntheses of conjugated octadecadienoic acids

Preparation of α-Bromoketones and Thiazoles from Ketones with NBS and Thioamides in Ionic Liquids

Synthesis of Double C-Glycoside Analogue of sTn

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