Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins

Ferré-Filmon, Karine; Delaude, Lionel; Demonceau, Albert; Noels, Alfred F.

doi:10.1016/j.ccr.2004.02.011

Cited by 102 publications

(53 citation statements)

References 75 publications

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“…[22,23] The chemical synthesis of naturally occurring stilbenoid compounds, including resveratrol (3,4',5-trihydroxystilbene), has attracted a lot of attention recently, because of the remarkable physiological properties and potential therapeutic values of these phytoalexins. [24] Hence, we were pleased to note that the presence of a terminal methyl group on the C=C double bond of trans-anethole did not hinder the metathesis process. On the other hand, attempts to homocouple a-methylstyrene with complex 3a were completely unsuccessful.…”

Section: Catalytic Investigationsmentioning

confidence: 98%

Homobimetallic Ruthenium–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Catalytic Applications

et al. 2007

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where L = 1,3-bis(2,4,6-trimethylphenyl)imidazolin-2-ylidene (3a) or 1,3-bis(2,4,6-trimethylphenyl)-4,5-dichloroimidazolin-2-ylidene (3b), were isolated in high yields upon heating a toluene solution of [RuCl 2 A C H T U N G T R E N N U N G (p-cymene)] 2 with 1 equivalent of carbene ligand under an ethylene atmosphere. They were characterized by NMR and TGA. Their catalytic activity was investigated in the atom transfer radical polymerization of vinyl monomers. In the polymerization of methyl methacrylate, complex 3a displayed faster reaction rates than 3b and the related phosphine-based complex 2a (L = tricyclohexylphosphine), although control was more effective with the latter catalyst. When n-butyl acrylate or styrene served as monomer, a major shift of reactivity was observed between complex 2a that promoted controlled radical polymerization, and complexes 3a or 3b that favored metathetical coupling. Further homocoupling experiments with various styrene derivatives confirmed the outstanding aptitude of complex 3a (and to a lesser extent of 3b) to catalyze olefin metathesis reactions. Contrary to monometallic ruthenium-arene complexes of the [RuCl 2 A C H T U N G T R E N N U N G (p-cymene)(L)] type, the new homobimetallic species did not require the addition of a diazo compound or visible light illumination to initiate the ring-opening metathesis of norbornene or cyclooctene. When a,w-dienes were exposed to 3a or 3b, a mixture of cycloisomerization and ring-closing metathesis products was obtained in a non-selective way. Addition of a terminal alkyne co-catalyst enhanced the metathetical activity while completely repressing the cycloisomerization process. Thus, quantitative conversions of diethyl 2,2-diallylmalonate and N,N-diallyltosylamide were achieved within 2 h at room temperature using 2 mol % of catalyst precursor 3 a and 6 mol % of phenylacetylene.

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Section: Catalytic Investigationsmentioning

confidence: 98%

Homobimetallic Ruthenium–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Catalytic Applications

et al. 2007

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“…Due to its outstanding stereoselectivity, Heck coupling is of particular interest in the pharmaceutical chemistry [18] and has been demonstrated in both homogeneous and heterogeneous systems previously, including other MOFs [19][20][21][22][23]. To highlight the advantage of combining the MTV approach with postmodification, we investigated the Heck coupling reaction for the synthesis of resveratrol trimethyl ether, a pharmaceutically relevant precursor.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous heck coupling in multivariate metal–organic frameworks for enhanced selectivity

Brown

Jarenwattananon

Otto

et al. 2015

Catalysis Communications

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“…The latter results are promising in relation with the synthesis of resveratrol analogues. 21 With regard to the stereochemistry, it is well known that semistabilised ylides, such as benzyl ylides, usually yield mixtures of Z-and E-isomers. 22 In particular, the reactions with benzylidenetriphenylphosphorane and aromatic aldehydes are practically nonselective.…”

Section: Scheme 1 A-alkylation Of Ketones and Indirect Aza-wittig Reamentioning

confidence: 99%

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

Alonso¹,

Riente²,

Yus³

2009

Synlett

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Catalytic methods for the synthesis of stilbenes with an emphasis on their phytoalexins

Cited by 102 publications

References 75 publications

Homobimetallic Ruthenium–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Catalytic Applications

Homobimetallic Ruthenium–N‐Heterocyclic Carbene Complexes: Synthesis, Characterization, and Catalytic Applications

Heterogeneous heck coupling in multivariate metal–organic frameworks for enhanced selectivity

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

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