Stereoselective Synthesis of (<i>E</i>)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

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

doi:10.1002/ejoc.200500068

Cited by 57 publications

(36 citation statements)

References 54 publications

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“…In this case, the lack of reactivity was most likely due to the formation of a stabilized ruthenium-benzylidene species possessing a chelated methoxy ligand. [23,25] To expand the scope of homobimetallic ruthenium catalysis in olefin metathesis, we have examined the ROMP of two representative cycloalkenes in the presence of complexes 2a, 3a, and 3b (Table 3). Polymerizations of cyclooctene were carried out in chlorobenzene at 60 8C for 2 h using a monomer-to-catalyst ratio of 250.…”

Section: Catalytic Investigationsmentioning

confidence: 99%

“…Thus, trans-anethole is a prime starting material to access the important class of polyhydroxystilbenes via olefin metathesis. [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.…”

Section: Catalytic Investigationsmentioning

confidence: 99%

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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: 99%

Section: Catalytic Investigationsmentioning

confidence: 99%

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

et al. 2007

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“…Homo-alkene-alkene CM of was described [1211,1212]. (224) Ruthenium catalyzed alkene-alkene CM of styrenes [1213], 1-allyl-tetrahydro-␤-carboline and -tetrahydroquinoline [1214], propenoic esters [1215,1216], alkenylsilanes [283,1217], allyl trimethylsilane [1218], conjugated dienes [1219,1220], allyl cyanide [1221], acrylonitrile [1222], ethenylazulene [1223], N-allylpyrimidines [1224], terminal 1-en-4-ols [644] and ␤-hydroxyenones [1225] with terminal alkenes were described.…”

Section: Metathesis Reactionsmentioning

confidence: 99%

Transition metals in organic synthesis: Highlights for the year 2005

Söderberg

2008

Coordination Chemistry Reviews

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“…[14] Organozinc halides react with carbonyl compounds in the presence of the palladium(II) complex PdCl 2 (PPh 3 ) 2 and a silylating agent to give the corresponding (E)-stilbenes in good-to-excellent yields under mild conditions. [17][18][19][20] The metathesis transformations used extensively in total synthesis include ring-closing metathesis (RCM), cross-metathesis (CM), ring-opening metathesis (ROM), and ring-opening metathesis polymerization (ROMP). [15,16] The formation of carbon-carbon bonds is of vital importance in preparative organic processes from the synthesis of molecular models to macromolecular and nanomaterials science.…”

Section: Introductionmentioning

confidence: 99%

A Highly Stereoselective and Efficient Catalytic Approach for the Synthesis of trans‐Stilbene–Arenes as π‐Conjugated Materials

2017

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The potential expansion of the variety of catalytic methods for carbon–carbon bond formation is explored in many research centers all over the world. In this work, we describe very precise and controlled catalytic transformations as useful tools for the synthesis of new trans‐π‐conjugated molecular organic compounds. The combination of Suzuki–Miyaura coupling and cross‐metathesis reactions is established as a simple and efficient method for the design of new (E)‐stilbenes in the presence of well‐defined transition‐metal catalysts at 0.0001–1 % loadings. All of the desired products are isolated in good‐to‐excellent yields (up to 96 % isolated yield) with high purity.

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Stereoselective Synthesis of (E)‐Hydroxystilbenoids by Ruthenium‐Catalyzed Cross‐Metathesis

Cited by 57 publications

References 54 publications

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

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

Transition metals in organic synthesis: Highlights for the year 2005

A Highly Stereoselective and Efficient Catalytic Approach for the Synthesis of trans‐Stilbene–Arenes as π‐Conjugated Materials

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