Introducing deep eutectic solvents as biorenewable media for Au(<scp>i</scp>)-catalysed cycloisomerisation of γ-alkynoic acids: an unprecedented catalytic system

Rodríguez-Álvarez, María J.; Vidal, Cristian; Dı́ez, Josefina; García‐Álvarez, Joaquín

doi:10.1039/c4cc05904b

Cited by 65 publications

(30 citation statements)

References 36 publications

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“…The catalytic system could be recycled up to four times without depletion on the yield but doubling the reaction times, under aerobic conditions. [129] Scheme 53. Gold catalyzed reactions.…”

Section: Organometallic Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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This microreview summarizes the use of deep eutectic solvents (DES) and related melts in Organic Synthesis. This type of solvents combine the great advantages of other proposed environmentally benign alternative solvents, such as low toxicity, high availability, low inflammability, high recyclability, low volatility and low price, avoiding many disadvantages of these neoteric media. The fact that many of the components of the mixture come directly from Nature assures their biodegradability and renewability. The classification and distribution of the reactions in different sections along this microreview, as well as the emphasis paid to their scope, easily allows a general reader to understand the actual state of art, and the great opportunities opened, not only for academic proposes but also for industry.

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Section: Organometallic Reactionsmentioning

confidence: 99%

Deep Eutectic Solvents: The Organic Reaction Medium of the Century

et al. 2016

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“…Acetylation of monosaccharides in ChCl-ZnCl 2 (1:2), shown for α-1-methoxyglucose. Other transformations catalyzed by transition metals are the hydroformylation of 1-decene in cyclodextrin-DMU catalyzed by Rh [160] and the cycloisomerization of γ-alkynoic acids, [161] (Z)-enynols, [162] and alkynyl amides [163] in ChCl-based DES catalyzed by Au I . [125] However, the sensitivity of these chloroaluminate ILs to water may lead to deactivation.…”

Section: Application In Organic Synthesismentioning

confidence: 99%

“…[155,156] [155,156] Furthermore, palladium catalyzed C-C coupling reactions were performed in DES based on saccharides and DMU or urea, including the Stille, [157] Heck, Sonogashira, [158] and Suzuki [159] coupling. Other transformations catalyzed by transition metals are the hydroformylation of 1-decene in cyclodextrin-DMU catalyzed by Rh [160] and the cycloisomerization of γ-alkynoic acids, [161] (Z)-enynols, [162] and alkynyl amides [163] in ChCl-based DES catalyzed by Au I .…”

Section: Application In Organic Synthesismentioning

confidence: 99%

Organic Synthesis without Conventional Solvents

Obst

König

2018

Eur J Org Chem

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Organic synthesis without an organic solvent is still the exception. In this microreview, we discuss and compare different synthetic methods that proceed in the absence of conventional organic solvents. This includes solvent‐free methods in solids (mechanochemistry and solid‐state photochemistry), and in neat liquids (thermal and photocatalytic), as well as the application of unconventional solvents, such as ionic liquids and deep‐eutectic solvents. The different approaches are briefly introduced and examples illustrate their specific advantages, followed by a critical discussion of their limitations. Some methods have the intrinsic benefits of solvent‐free operation, such as avoiding solubility problems and side‐reactions with the solvent. However, every method has specific advantages and the demand of the synthetic application is crucial for selecting the best technique.

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“…The same conditions were used by Marchal et al to transform o ‐alkynylbenzoic acids and 2‐(2‐ethynylphenyl)acetic acids into the corresponding alkylidenelactones . More recently, a water‐soluble Au III –NHC complex, dispersed thiol‐stabilized gold nanoparticles in the pores of siliceous mesocellular foam and a gold catalyst in combination with deep eutectic solvents were applied in the catalytic cycloisomerization of γ‐alkynoic acids. Nevertheless, the gold‐catalyzed cycloisomerization of alkyne‐containing amino acids was scarcely explored.…”

Section: Introductionmentioning

confidence: 99%