Magnetic nano-graphene oxide-supported molybdenum (Fe3O4/GO-Mo) as a green, efficient, and recyclable catalyst for synthesis of β-hydroxy hydroperoxides

Liu, Yuheng; Hu, Hai‐Chuan; Ma, Zichuan; Dong, Yuhua; Wang, Can; Pang, Yunmeng

doi:10.1007/s00706-017-2092-8

Cited by 15 publications

(8 citation statements)

References 49 publications

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“…On the contrary,u nder heterogeneous conditions on the surfaceo ft he catalyst, peroxides, including hydrogen peroxide, tend to decompose. [20] There are only few syntheses of peroxidesu nder heterogeneous conditions proposed for more than ac entury: heminalb ishydroperoxides, [14q,n, 21] b-hydroxy-hydroperoxides, [22] 1,2,4-trioxanes, [23] peroxides from b-dicarbonyl compounds, [24] and b,d'triketones. [13b] This work discloses am ethodology for the selectivep eroxidation of 1,3-and 1,5-diketones under heterogeneous conditions.…”

Section: Introductionmentioning

confidence: 99%

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Yaremenko

Radulov

Belyakova

et al. 2020

Chemistry A European J

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The catalyst H3+xPMo12−x+6Mox+5O40 supported on SiO2 was developed for peroxidation of 1,3‐ and 1,5‐diketones with hydrogen peroxide with the formation of bridged 1,2,4,5‐tetraoxanes and bridged 1,2,4‐trioxolanes (ozonides) with high yield based on isolated products (up to 86 and 90 %, respectively) under heterogeneous conditions. Synthesis of peroxides under heterogeneous conditions is a rare process and represents a challenge for this field of chemistry, because peroxides tend to decompose on the surface of a catalyst . A new class of antifungal agents for crop protection, that is, cyclic peroxides: bridged 1,2,4,5‐tetraoxanes and bridged ozonides, was discovered. Some ozonides and tetraoxanes exhibit a very high antifungal activity and are superior to commercial fungicides, such as Triadimefon and Kresoxim‐methyl. It is important to note that none of the fungicides used in agricultural chemistry contains a peroxide fragment.

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Section: Introductionmentioning

confidence: 99%

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Yaremenko

Radulov

Belyakova

et al. 2020

Chemistry A European J

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“…In 2017, a very similar work than reported earlier by the Zhang group (from the same university) has described the conversion of epoxides into β-hydroxy hydroperoxides using ethereal H 2 O 2 catalyzed by magnetic nano-graphene oxidesupported molybdenum (Fe 3 O 4 /GOÀ Mo). [66] The preparation of the catalytic system was not described in this study but was previously reported and characterized in another context. [67] An excess amount of H 2 O 2 (5 equivalents) and using a 20 mol% catalyst loading of Fe 3 O 4 /GOÀ Mo at room temperature were found to be the optimal conditions.…”

Section: Ring-opening Of Epoxides With H 2 Omentioning

confidence: 99%

The Chemistry of β‐Hydroxy Hydroperoxides

Louvel

Miguel

et al. 2021

Eur J Org Chem

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β-Hydroxy hydroperoxides (β-hydroperoxy alcohols) are interesting chemical platforms, notably for the preparation of 1,2,4trioxanes, that are key features of numerous bioactive products such as artemisinin. In this review, the main synthetic methods to prepare β-hydroxy hydroperoxides are presented, such as the photooxidation of allylic alcohols with singlet oxygen and the ring-opening of epoxides with H 2 O 2 . The main applications of β-hydroxy hydroperoxides are also detailed, including their peracetalization to 1,2,4-trioxanes, their use as epoxidating agents and their fragmentation to carbonyl compounds. A final section is dedicated to the general characteristics and practical aspects of β-hydroxy hydroperoxides, including their stability, safety and characterization through spectroscopic means.

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“…[24] Early works used Brønsted acids as catalysts such as HClO 4 [25] and CF 3 CO 2 H. [26] Moreover, Lewis acids such as SnCl 4 , [27] SbCl 3 /SiO 2 , [28] and phosphomolybdic acid [29] (PMA) were also used to promote the reaction. Recently, magnetic nanoparticle-supported phosphomolybdate [30] and nano-graphene oxide-supported molybdenum [31] were reported as recoverable and recyclable catalysts. Although these methods provide β-hydroxy hydro-peroxides with high yields, they require the use of neat or ethereal H 2 O 2 .…”

Section: Preparation Of Fatty β-Hydroxy Hydroperoxidesmentioning

confidence: 99%

Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β‐Hydroxy Hydroperoxides**

Miguel

Lemaire

et al. 2020

ChemSusChem

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The ring-opening of epoxidized methyl oleate by aqueous H 2 O 2 has been studied using tungsten and molybdenum catalysts to form the corresponding fatty β-hydroxy hydroperoxides. It was found that tungstic acid and phosphotungstic acid gave the highest selectivities (92-93 %) towards the formation of the desired products, thus limiting the formation of the corresponding fatty 1,2-diols. The optimized conditions were applied to a range of fatty epoxides to give the corresponding fatty βhydroxy hydroperoxides with 30-80 % isolated yields (8 examples). These species were fully characterized by 1 H and 13 C NMR spectroscopy and HPLC-HRMS, and their stability was studied by differential scanning calorimetry. The thermal cleavage of the β-hydroxy hydroperoxide derived from methyl oleate was studied both in batch and flow conditions. It was found that the thermal cleavage in flow conditions gave the highest selectivity towards the formation of aldehydes with limited amounts of byproducts. The aldehydes were both formed with 68 % GC yield, and nonanal and methyl 9-oxononanoate were isolated with 57 and 55 % yield, respectively. Advantageously, the overall process does not require large excess of H 2 O 2 and only generates water as a byproduct.

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Magnetic nano-graphene oxide-supported molybdenum (Fe3O4/GO-Mo) as a green, efficient, and recyclable catalyst for synthesis of β-hydroxy hydroperoxides

Cited by 15 publications

References 49 publications

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

Catalyst Development for the Synthesis of Ozonides and Tetraoxanes Under Heterogeneous Conditions: Disclosure of an Unprecedented Class of Fungicides for Agricultural Application

The Chemistry of β‐Hydroxy Hydroperoxides

Biobased Aldehydes from Fatty Epoxides through Thermal Cleavage of β‐Hydroxy Hydroperoxides**

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