Acceleration of Organic Reactions through Aqueous Solvent Effects

Pirrung, Michael C.

doi:10.1002/chem.200500959

Cited by 342 publications

(123 citation statements)

References 24 publications

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“…The reaction with nonlabeled 1-octanal (1 b), 1-octanoic acid (2 b), and ethyl isocyanoacetate (3) or pentyl isocyanide (4) in H 2 18 O, gave the Passerini product with one incorporated 18 O as the major product (Table 3, entries 4 and 5; 5 b and 6 b, respectively). For comparison, the Passerini reaction products showed no incorporation of 18 O upon stirring "on H 2 18 O" in the presence of acid.…”

Section: Nelly Shapiro and Arkadi Vigalok*mentioning

confidence: 98%

Highly Efficient Organic Reactions “on Water”, “in Water”, and Both

Shapiro,

Vigalok

2008

Angew Chem Int Ed

191

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Wet, wet, wet: Hydrophobic aldehydes are cleanly oxidized upon stirring with water in air. Addition of hydrophobic isocyanides to aqueous suspensions of such aldehydes results in the formation of Passerini reaction products, with the aldehyde being the source of both carbonyl and ester functions. Partially water‐soluble reagents reacted slower than water‐insoluble ones. Isotope labeling studies show that water participates in these “on water” reactions.

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Section: Nelly Shapiro and Arkadi Vigalok*mentioning

confidence: 98%

Highly Efficient Organic Reactions “on Water”, “in Water”, and Both

Shapiro,

Vigalok

2008

Angew Chem Int Ed

191

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“…Water is known to be the cheapest, environmentally benign, safe and most abundant compound on the earth's surface; and it has attracted a great deal of attention from a green chemistry perspective [33][34][35][36][37][38][39][40][41][42][43]. In addition, water also holds some unique physical and chemical properties, such as high surface tension, hydrogen bonding capability, high dielectric constant and high cohesive energy density [44][45][46]. In nature, both type I and type II aldolases catalyze the direct aldol reaction in an aqueous environment [47].…”

Section: Introductionmentioning

confidence: 99%

Ionic Liquid Immobilized Organocatalysts for Asymmetric Reactions in Aqueous Media

Qiao

Headley

2013

Catalysts

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Ionic liquids are organic salts with melting points typically below ambient or reaction temperature. The unique combination of physical properties of ionic liquids, such as lack of measurable vapor pressure, high thermal and chemical stability, make them ideal to be used as reusable homogenous support for catalysts. In addition, the solubility of ionic liquids in various reaction media can be controlled and easily fine-tuned by modification of the structures of their cations and anions. As a result, ionic liquid immobilized organocatalysts are very effective in aqueous media and can be separated easily from organic solvents, as well as aqueous phases by simply adjusting the polarity of the media. Ionic liquid immobilized organocatalysts are not only very versatile compounds that are effective catalysts for a wide spectrum of reactions, but are also environmentally friendly and recyclable organocatalysts. Herein, we provide a summary of the past decade in the area of asymmetric catalysis in aqueous media for a wide variety of reactions in which ionic liquid and related ammonium salt immobilized organocatalysts are used.

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“…Both water-soluble PdA C H T U N G T R E N N U N G (OAc) 2 [P(m-C 6 H 4 SO 3 Na) 3 ] 2 and water-insoluble PdA C H T U N G T R E N N U N G (OAc) 2 A C H T U N G T R E N N U N G (PPh 3 ) 2 are effective catalysts for this transformation [Eq. (6)]. [48] When organic salts are used as a coupling reagent, water is a preferred reaction medium.…”

Section: Introductionmentioning

confidence: 99%