Oxone–acetone mediated syn-dioxygenation of benzo-fused olefins

Phatake, Ravindra S.; Ramana, Chepuri V.

doi:10.1016/j.tetlet.2015.03.022

Cited by 13 publications

(8 citation statements)

References 91 publications

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“…[65][66][67] In this context, in the year 2015, Phatake and Ramana studied intensively syn-dioxygenation using oxoneacetone combination under mild and easy to handle conditions to provide the 1,3-dioxolanes 87 a-f from indene and dihydronaphthalene derivatives, described in the Scheme 24. [55]…”

Section: Syn-dioxygenation Of the Benzo-fused Olefinic Systemsmentioning

confidence: 99%

“…In 2013, Che's group performed epoxidation of olefins having internal/external double bonds to give the corresponding products ( 30 , 57 – 59) in the presence of [Fe III (Tp) 2 ] + /[Fe III (Me 3 tacn)(R‐acac)Cl] + and oxone using a solvent mixture of CH 3 CN/H 2 O or acetone/H 2 O at room temperature [54] . In a separate study, Phatake and Ramana reported epoxidation of the alkenes using oxone‐acetone in 2015 [55] . Whileas, the epoxidation of styrene to give (30) was performed by Cai et al .…”

Section: Functionalization Of Olefinsmentioning

confidence: 99%

“…Notably, almost all of these methods suffer from toxicity, instability, explosive nature of reagents, generation of unsafe waste products and difficulties to remove the metal impurities from the required products [65–67] . In this context, in the year 2015, Phatake and Ramana studied intensively syn ‐dioxygenation using oxone‐acetone combination under mild and easy to handle conditions to provide the 1,3‐dioxolanes 87 a – f from indene and dihydronaphthalene derivatives, described in the Scheme 24 [55] …”

Section: Functionalization Of Olefinsmentioning

confidence: 99%

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Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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Presently, the major cornerstone of the research community is to develop green as well as sustainable protocols involving inexpensive catalysts and/or reagents without the usage of hazardous solvents under globally friendlier conditions in order to shelter both mankind and environment. Therefore, needless to say, there is always a supreme need to surrogate the older, costlier and unsafe strategies with the novel economically inexpensive and environmental benign ones. To this context, in recent past, oxone® (triple salt), a very cheap oxidizing agent having the chemical formula 2KHSO5 ⋅ KHSO4 ⋅ K2SO4 and enwrapped with the unique characteristics like easy handling, non‐toxic, safe, eco‐friendly, non‐polluting, stable, and nicely soluble in water, in addition to its utility for large‐scale synthesis etc. Bearing the importance of this versatile reagent in mind, we envisioned to update the recent advances made in this direction. Consequently, in this particular review article, the developments made in the arena of oxone chemistry covering from 2013 to 2020 have been revealed as no report appeared in the literature after a wonderful Chem. Rev. published by the group of Hussain in 2013. Herein, a comprehensive detail of a variety of oxidative transformations along with the complete plausible mechanistic steps have been exposed. For sure, present review would be a very helpful tool to the scientific community not only working in the area of organic synthesis but also to the researchers working in other branches of science and technologies as well.

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Section: Syn-dioxygenation Of the Benzo-fused Olefinic Systemsmentioning

confidence: 99%

Section: Functionalization Of Olefinsmentioning

confidence: 99%

Section: Functionalization Of Olefinsmentioning

confidence: 99%

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Applications of Oxone® in Organic Synthesis: An Emerging Green Reagent of Modern Era

2022

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“…2,1-Benzisoxazoles were obtained in good to high yields from substrates bearing aryl, vinyl or alkyl R 3 groups. Although, a variety of olefins, including chalcones, were cleaved oxidatively to give the corresponding acids with Oxone in acetonitrile/water mixture (1:1, v/v) at reflux temperature, 30 and Oxone/acetone-mediated syn-dioxygenation of benzo-fused olefins has been described, 31 our mild reaction conditions were compatible with the presence of the C=C double bond, accomplishing an alternative and very efficient synthesis of the corresponding 3-(β-styryl)-2,1benzisoxazoles 9 3d-k from the readily available o-amino-chalcones 1d-k (Table 2, entries 4-11). Interestingly, the procedure was extended to the synthesis of (E)-3-[(2-furan-2-yl)vinyl]benzo[c]isoxazole (3j) (Table 2, entry 10).…”

Section: Syn Thesismentioning

confidence: 99%

Synthesis of 3-Substituted 2,1-Benzisoxazoles by the Oxidative Cyclization of 2-Aminoacylbenzenes with Oxone

et al. 2016

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An efficient approach to the synthesis of 2,1-benzisoxazoles through direct construction of the N–O bond by the chemoselective oxidation of 2-aminoacylbenzenes with Oxone is described. This alternative methodology is characterized by its simple and transition-metal-free conditions and good functional group compatibility utilizing Oxone as a green oxidant instead of hypervalent iodine compounds. Moreover, this new procedure simplifies the number of steps compared to the previously reported procedure by circumventing the use of 2-azido-substituted aryl ketones

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“…8 Very recently, we have shown that the combination of oxone-acetone, which is well established for the olefin epoxidation reactions, can be used for the cis-dioxygenation of the benzofused olefins leading to a cis-vicinol diol protected as its acetonide. 9 We have come across this unusual dioxygenation accidently, while carrying out the preparation of the known indene oxide on multi-gram scales employing the oxone-acetone combination for the epoxidation. A set of two side products (2-3%), namely the indan-2-one 3a and the acetonide 4a along with the required epoxide 2a were obtained under the described conditions (Fig.…”

mentioning

confidence: 99%