Oxidation of Tertiary Aromatic Alcohols to Ketones in Water

Chen, Dengfeng; Zhang, Yuchen; Pan, Xingyu; Wang, Fei; Huang, Shenlin

doi:10.1002/adsc.201800612

Cited by 25 publications

(10 citation statements)

References 58 publications

(13 reference statements)

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“…Chen et al have also sought to exploit rosin as a potential source of raw materials for the synthesis of surfactants, see Figure 27 . 258 DAPGS-750-M is structurally related to APGS-550-M in that it is also derived from abietic acid. Aqueous-micellar conditions using this surfactant have allowed for β-scission of −CH 3 from a range of aromatic tertiary alcohols to give corresponding ketones.…”

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

“…One potential reason for this is due to the different shape, size, and distribution of the DAPGS micelles when compared to other surfactants examined in this publication. 258 A variety of acetophenone-like molecules were prepared from the corresponding tertiary alcohols in moderate to excellent yields, though anilines were not tolerated at all. Furthermore, bulky β-carbon groups were preferentially eliminated in preference of methyl groups.…”

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

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Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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Dipolar aprotic and ethereal solvents comprise just over 40% of all organic solvents utilized in synthetic organic, medicinal, and process chemistry. Unfortunately, many of the common “go-to” solvents are considered to be “less-preferable” for a number of environmental, health, and safety (EHS) reasons such as toxicity, mutagenicity, carcinogenicity, or for practical handling reasons such as flammability and volatility. Recent legislative changes have initiated the implementation of restrictions on the use of many of the commonly employed dipolar aprotic solvents such as dimethylformamide (DMF) and N -methyl-2-pyrrolidinone (NMP), and for ethers such as 1,4-dioxane. Thus, with growing legislative, EHS, and societal pressures, the need to identify and implement the use of alternative solvents that are greener, safer, and more sustainable has never been greater. Within this review, the ubiquitous nature of dipolar aprotic and ethereal solvents is discussed with respect to the physicochemical properties that have made them so appealing to synthetic chemists. An overview of the current legislative restrictions being imposed on the use of dipolar aprotic and ethereal solvents is discussed. A variety of alternative, safer, and more sustainable solvents that have garnered attention over the past decade are then examined, and case studies and examples where less-preferable solvents have been successfully replaced with a safer and more sustainable alternative are highlighted. Finally, a general overview and guidance for solvent selection and replacement are included in the Supporting Information of this review.

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Section: Selection Of Alternative Solventsmentioning

confidence: 99%

Section: Selection Of Alternative Solventsmentioning

confidence: 99%

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

et al. 2022

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“…A variety of such nonionic benign by design surfactants is all considered PEGylated amphiphilic species, with or without a linker. TPGS-750-M [24], PQS [25], SPGS-550-M [26], Coolade [27], DAPGS-750-M [28], APGS-550-M [29], MC-1 [30], PTS [31], SMPS [32], BTBT-750-M, PiNAP-750-M [33], TPGlite [34], or PS-750-M [35] are some of the most studied excipients (Scheme 1). They have been demonstrated to be extremely versatile, most notably TPGS-750-M and PS-750-M, and shown to function as suitable surrogates to reprotoxic polar aprotic solvents, thus offering a real opportunity to phase out such solvents.…”

Section: Water Chemistry Enabled By Surfactantsmentioning

confidence: 99%

Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

Hauk

Wencel‐Delord

Ackermann

et al. 2021

Current Opinion in Colloid & Interface Science

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“…The impressive potentialities of designer surfactants developed by Lipshutz spurred several other research groups to design, synthesize and test new surfactants for catalytic applications. An interesting new surfactant based on the dehydroabietinol-polyethyleneglycol-succinate monomethyl ether structure called DAPGS-750-M, as a potential alternative to the commercially available TPGS-750-M, was proposed based on the hydrophobic core of rosin functionalized with a PEG unit to be employed for the oxidation of tertiary alcohols with β-scission mediated by AgNO 3 , K 2 S 2 O 8 and Bi(OTf) 3 leading to ketones in water (Scheme 7) [120]. The reaction was possible under mild experimental conditions, for a wide range of substrates with the simple in-flask recycling of the aqueous phase after product isolation.…”

Section: Other Designer Surfactantsmentioning

confidence: 99%

Surfactant for better tomorrow: applied aspect of surfactant aggregates from laboratory to industry

et al. 2019

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Surfactant is a special kind of amphiphilic compound composed of water-loving and hating parts. The remarkable physical properties like interfacial tension, wettability, emulsifying and dispersing ability make the surfactant accessible for numerous applications from laboratory to commercial products. In recent years, the commercial applications of surfactant have led to greater relevance on account of the environmental concerns and market pressures of this compound. The utility of surfactants in global market increases steadily since its formulation with several beneficial aspects in pharmaceutical, detergent, cosmetic, paint, food science, gas hydrate, nanotechnology, petroleum recovery, bioremediation, chemical transformation and drug delivery. This review briefly discusses the applied aspect of surfactants in diverse area as well as catalytic effect of micelle in organic reactions from the recent literature survey. The trend of increasing use of bioderived surfactants in the modern field of research is also considered in this report. The recent advancement of surfactant-based organic transformations has been emphasized with the role of surfactant aggregates in course of different organic reactions.

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Oxidation of Tertiary Aromatic Alcohols to Ketones in Water

Cited by 25 publications

References 58 publications

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Replacement of Less-Preferred Dipolar Aprotic and Ethereal Solvents in Synthetic Organic Chemistry with More Sustainable Alternatives

Organic synthesis in Aqueous Multiphase Systems — Challenges and opportunities ahead of us

Surfactant for better tomorrow: applied aspect of surfactant aggregates from laboratory to industry

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