Reactivity of Carbenes in Aqueous Nanomicelles Containing Palladium Nanoparticles

Duong, Uyen T.; Gade, Amol B.; Plummer, Scott; Gallou, Fabrice; Handa, Sachin

doi:10.1021/acscatal.9b04175

Cited by 32 publications

(41 citation statements)

References 38 publications

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“…15, right) imitates amide solvents (e.g., DMF and NMP), accommodating substrates with moderate-to-high polarities, e.g., nitroalkanes 63 and hydrazones. 64 Hence, this leads to better stirring, higher conversions, and thus, improved yields. Most importantly, from the green chemistry perspective, this technology enables reactions to take place in water under ambient conditions involving polar compounds to the exclusion of toxic dipolar aprotic organic solvents.…”

Section: (G) Water Sculpting Effect On Nanoparticlesmentioning

confidence: 99%

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

et al. 2021

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Section: (G) Water Sculpting Effect On Nanoparticlesmentioning

confidence: 99%

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

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“…Cross‐coupling chemistry relies on the high loading of expensive Pd catalysts. Recently, Handa and co‐workers developed catalytically active palladium nanoparticles, which are recyclable, easy to synthesize, compatible for chemistry in water, and derived from palladium and inexpensive PPh 3 (Scheme ) . The catalyst is specially designed for the reactivity of carbenes in the micelles of PS‐750‐M in water.…”

Section: Transformations In Green Solventsmentioning

confidence: 99%

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

et al. 2020

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Scheme2.Heck-Mizorokir eaction in g-valerolactone.Scheme3.Synthesis of 1-butyl-3-methylimidazoliumchloride using scCO 2 .Scheme1.Suzuki-Miyaura coupling in 2-Me-THF.Scheme4.Improved synthetic route to sildenafilc itrate.Scheme5.Improved synthetic route to ibuprofen.Scheme6.Cu-catalyzed cyclopropanation.Scheme17. Amination in synthesis of efaproxiral.Scheme15. Peptide couplingsint he synthesis of sildenafil and sunitinib.Scheme16. Amide couplings in water.Scheme20. Couplings of unactivated (iso)quinolines in PS-750-M.Scheme21. PS-750-M as ar eplacement for toxic polar-aprotic solvent for sp 2 -sp 3 couplings.Scheme22. Recyclable palladium nanoparticles in PS-750-M for olefins ynthesis through carbene insertion.Scheme23. Drugmolecules containingC ÀNb onds.Scheme24. Recyclable bimetallic nanoparticles for sustainable Buchwald-Hartwig aminations in water.Scheme25. Ac omparison between chemistryinw ater versus chemistryino rganic solvents (Novartis Pharmaceuticals).

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“…Since the initial publication, the surfactant has been used to enable aqueous reactions including S N Ar, 239 α-arylations, 240 fluorination of indoles, 241 and Pd carbene-mediated insertions. 242 …”

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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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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Reactivity of Carbenes in Aqueous Nanomicelles Containing Palladium Nanoparticles

Cited by 32 publications

References 38 publications

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

Water as the reaction medium in organic chemistry: from our worst enemy to our best friend

A Glimpse into Green Chemistry Practices in the Pharmaceutical Industry

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

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