Chiral Surfactant-Type Catalyst for Asymmetric Reduction of Aliphatic Ketones in Water

Li, Jiahong; Yu, Tengfei; Wang, Qiwei; Li, Xuefeng; Liu, Cun; Zhang, Xiaomei; Zhu, Jin; Li, Liangchun; Deng, Jingen

doi:10.1021/ja308357y

Cited by 131 publications

(97 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Many of these compounds comprise com plexes with Cp (cyclopentadienyl anion) due to their sufficient stability in protonic solvents, ultimately in water. Li et al described a Rh Cp I SURF used in enantioselective catalysis [42]. An inverted, hydropho bic hydrophilic motif was presented by Shen et al with an I SURF con taining ferrocene in the hydrophobic moiety [43].…”

Section: Amphiphilic Ligands With Coordinated Metalsmentioning

confidence: 99%

Amphiphilic hybrids containing inorganic constituent: More than soap

Polarz

Odendal

Hermann

et al. 2015

Current Opinion in Colloid & Interface Science

View full text Add to dashboard Cite

a b s t r a c t Keywords:Self-assembly Polyoxometalates Organic-inorganic hybrids Amphiphiles Janus particles Amphiphiles and surfactants are indispensable compounds in industry, scientific research and everyday life, such as emulsification agents, detergents, etc. The vast majority of currently used amiphiphiles are organic in nature, and are composed of two molecular parts joined together, one hydrophilic and one hydrophobic. The current article highlights some of the recent developments in the emerging field of hybrid amphiphiles, focusing on systems with at least one inorganic constituent. Different classes of amphiphiles can be defined, depending on if the inorganic entity is molecular or has particle character, and depending on the strength of interaction between the inorganic and organic phase. It is seen that in addition to typical amphiphilic properties, most importantly the formation of self assembled structures like micelles or lyotropic liquid crystals, the hybrid amphiphiles exhibit additional, functional features like special magnetic or catalytic properties. Ultimately, systemic features can be observed, leading to the emergence of new properties which none of the constituents of hybrid amphiphile could have on its own.

show abstract

Section: Amphiphilic Ligands With Coordinated Metalsmentioning

confidence: 99%

Amphiphilic hybrids containing inorganic constituent: More than soap

Polarz

Odendal

Hermann

et al. 2015

Current Opinion in Colloid & Interface Science

View full text Add to dashboard Cite

show abstract

“…However, liquid inorganic acids inevitably have many disadvantages, such as corrosion of equipment, troublesome product separation and environmental pollution (4); and solid acids have also shown some disadvantages, including low activity, easy deactivation and adsorption of products (3,5). To address the drawbacks of both liquid and solid acids, a novel catalytic system, for example, colloidal dispersion or reverse micelles, formed by Brønsted acidsurfactant-combined catalyst, has been reported (6). For example, Kabayashi et al reported dodecylbenzene sulfonic acid (DBSA)-catalyzed esterification of carboxylic acids and alcohols in water (7,8).…”

Section: Introductionmentioning

confidence: 99%

Esterification synthesis of ethyl oleate catalyzed by Brønsted acid–surfactant-combined ionic liquid

Zheng

Yang

et al. 2017

Green Chemistry Letters and Reviews

View full text Add to dashboard Cite

ABSTRACT3-(N,N-dimethyldodecylammonium) propanesulfonic acid hydrogen sulfate [HSO 4 ]), a Brønsted acidic-surfactant-combined ionic liquid, was successfully prepared from cheap materials and applied to catalyze the esterification synthesis of ethyl oleate using oleic acid and ethanol as precursors. The produced condition of oleic acid ethyl ester was optimized including the amount of catalyst, reaction time, molar ratio and content of water. Under optimal condition (ethanol to oleic acid molar ratio, 3:1; amount of the catalyst, 5 wt% (based on the mass of oleic acid); reaction time, 3 h; reaction temperature, 78°C; and content of water, 0.4 wt%), the conversion of oleic acid was over 97%. Due to the reverse micelles formed by [HSO 4 ], the microreactor not only promoted the esterification toward the desired side of the ester, but also avoided the hydrolysis of ester. Moreover, the [SB3-12][HSO 4 ] could be reused by a simple decantation separating process and noticeable loss of catalytic activity was not observed even after being recycled for five cycles. The green system offers several advantages, such as excellent yield, efficient catalytic activity, free-solvent and simple operational procedure. ARTICLE HISTORY

show abstract

“…In 2001 the first example of Ru(II)-catalyzed ATH of ketones with HCO 2 Na as a hydride source in aqueous media was reported [17]. Since this discovery, a number of water-soluble ligands and catalysts have been developed for ATH in aqueous media providing the reduction products in high conversion yields and enantioselectivities [18][19][20][21][22][23][24][25][26]. However, a major problem associated with these catalytic systems is that the low substrate/catalyst (S/C) ratio (normally S/C = 100) and large excess amounts of hydride donor (≥ 5 equiv.…”

Section: Introductionmentioning

confidence: 99%