One-Pot Synthesis of Stilbenes
from Alcohols through a Wittig-Type Olefination Reaction
Promoted by Nickel Nanoparticles

Alonso, Francisco; Riente, Paola; Yus, Miguel

doi:10.1055/s-0029-1217333

Cited by 21 publications

(3 citation statements)

References 11 publications

(12 reference statements)

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“…24 We have recently reported a novel synthesis of stilbenes, from benzyl alcohols as phosphorus ylide partners, through a one-pot Wittig-type olefination reaction promoted by nickel nanoparticles. 25 Resveratrol, DMU-212, and analogues have been synthesised using this methodology. 26 The precursor of the target molecule, dehydrobrittonin A, is a symmetrically-substituted highly polymethoxylated stilbene that could be synthesised from only one starting material (Scheme 3).…”

Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Transfer hydrogenation of olefins catalysed by nickel nanoparticles

2009

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a b s t r a c tNickel nanoparticles have been found to effectively catalyse the hydrogen-transfer reduction of a variety of non-functionalised and functionalised olefins using 2-propanol as the hydrogen donor. The heterogeneous process has been shown to be highly chemoselective for certain substrates, with all the corresponding alkanes being obtained in high yields. A synthesis of the natural dihydrostilbene brittonin A is also reported based on the use of nickel nanoparticles.

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Section: U N C O R R E C T E D P R O O Fmentioning

confidence: 99%

Transfer hydrogenation of olefins catalysed by nickel nanoparticles

2009

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“…Alonos et al. reported the use of nickel nano particles for the acceptorless dehydrogenative coupling of alcohols with semi‐stabilized ylides [9] . More recently, Milstein and co‐workers described the selective synthesis of alkenes by the ruthenium catalyzed acceptorless dehydrogenative coupling of alcohols with in situ generated, non‐stabilized ylides under homogenous conditions [10] .…”

Section: Introductionmentioning

confidence: 99%

Selective Construction of C−C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Liu

Werner

2020

Adv Synth Catal

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Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon‐carbon single (C−C) and carbon‐carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C−C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one‐pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C−C and C=C bond formation. Mechanistic studies suggest that the C−C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway.

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“…Amongst nanocatalysts, nickel nanoparticles have emerged as potent eco-friendly catalysts owing to their unique recyclability properties which allow them to be retrieved with ease by using a simple magnet after completion of a reaction and then reused multiple times without compromising the yield of the desired products. This has been exploited for the chemo-selective oxidative coupling of thiols, 2 the hydrothermal Heck reaction, 3 a-alkylation of methyl ketones, 4 reduction of aldehydes and ketones, 5a-c the transfer hydrogenation reaction, 6 simple olefin hydrogenation, 7 Wittig-type olefination for the synthesis of stilbenes from alcohol 8 and as supports for hydrogen adsorption. 9 Nanocatalysis of multicomponent reactions (MCRs) has also become considerably important these days due to its strategic advantages over conventional synthetic methods.…”

Section: Introductionmentioning

confidence: 99%

Nickel nanoparticles assisted regioselective synthesis of pyrazoloquinolinone and triazoloquinazolinone derivatives

et al. 2015

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Biologically important pyrazoloquinolinone and triazoloquinazolinone derivatives were synthesized by the condensation reaction of 3-amino-1H-1,2,4-triazole/3-amino-5-methyl-1H-pyrazole, dimedone and aryl aldehydes using catalytic amount of magnetically retrievable nickel nanoparticles under reflux condition. This protocol eliminates the usage of toxic reagents, complex work-up conditions, etc., with the added benefit of reusability of the catalyst without compromising the yield or purity of the product. Results and discussionOur present work deals with the synthesis of triazoloquinazolinones/pyrazoloquinolinones through a simple method in

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One-Pot Synthesis of Stilbenes from Alcohols through a Wittig-Type Olefination Reaction Promoted by Nickel Nanoparticles

Abstract: A series of stilbenes has been synthesised in one pot from benzyl alcohols and benzylidenetriphenylphosphorane through a Wittig-type olefination reaction in the presence of nickel nanoparticles.

Cited by 21 publications

References 11 publications

Transfer hydrogenation of olefins catalysed by nickel nanoparticles

Transfer hydrogenation of olefins catalysed by nickel nanoparticles

Selective Construction of C−C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Nickel nanoparticles assisted regioselective synthesis of pyrazoloquinolinone and triazoloquinazolinone derivatives

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