Ruthenium-catalyzed isomerization of homoallylic alcohols in water

Wang, Dong; Chen, Dongli; Haberman, John X.; Li, Chao‐Jun

doi:10.1016/s0040-4020(98)00252-x

Cited by 41 publications

(10 citation statements)

References 58 publications

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“…1‐Vinyl propargyl alcohols lead to the allylation of the nucleophile yielding the sterically less hindered ( Z )‐enynes in the case of tertiary substrates. A closely related ruthenium‐catalyzed transformation of allylic alcohols has been reported previously 7d,e. Internal substrates are not further converted.…”

Section: Resultsmentioning

confidence: 77%

Ruthenium‐Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols

Thies

Hrib

Haak

2012

Chemistry A European J

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Several ruthenium-catalyzed atom-economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox-coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway and depends on the alcohols' substitution pattern. Secondary substrates form alkenyl complexes by a 1,2-hydrogen shift, whereas the transformation of tertiary substrates involves allenylidene intermediates. 1-Vinyl propargyl alcohols are converted by a cascade allylation/cyclization sequence. The environmentally benign processes are of broad scope and allow the selective synthesis of highly functionalized pyrroles and indoles generating water as the only waste product.

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Section: Resultsmentioning

confidence: 77%

Ruthenium‐Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols

Thies

Hrib

Haak

2012

Chemistry A European J

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“…However, further increased amounts of catalyst to 7.2% lead a low selectivity (entry 6). Although the selectivity of catalyst 1 is slightly low when compared to the parent catalyst employing 4.0% Ru(II) metal reported in the literature (entry 4 versus entry 4 shown in bracket), 15 the selectivity employing 5.6% Ru(II) metal is better than that obtained using the corresponding Ru-SBA-15 catalyst without microwave irradiation (entry 5 versus entries 1-2), 11b and is nearly the same as that obtained using the corresponding Ru-SBA-15 catalyst and the parent homogeneous catalyst with microwave irradiation (entry 5 versus entries 1 and 2 shown in brackets). More importantly, the catalytic isomerization reaction under microwave irradiation can be completed at a much shorter reaction time (10 minutes).…”

Section: Resultsmentioning

confidence: 80%

Microwave-assisted tandem allylation-isomerization reaction catalyzed by a mesostructured bifunctional catalyst in aqueous media

et al. 2009

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A mesoporous silica-supported bifunctional Ti-Ru-SBA-15 catalyst with an ordered two-dimensional hexagonal mesostructure was prepared by postmodifying organometallic complexes RuCl 2 (PPh 3 ) 3 and Ti(O i Pr) 4 onto PPh 2 -SBA-15. During the tandem addition-isomerization reaction of benzaldehyde under microwave irradiation in aqueous media, the mesoporous silica-supported Ti-Ru-SBA-15 catalyst exhibited high catalytic activity (more than 97%) and selectivity (up to 96%). Such a catalyst could be recovered easily and used repetitively five times without significantly affecting its catalytic activity and selectivity.

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“…Besides the copper‐based ATRP process, the ruthenium‐catalyzed radical polymerization has also been investigated because RuCl 2 (PPh 3 ) 3 is insoluble in water and has been reported to have been successfully used for organic reactions44, 45 and polymerizations46, 47 in the presence of water and/or air on account of its low oxophilicity. The latexes used for polymerizations were prepared with the nanoprecipitation technique through the dissolution of the ruthenium complex with or without the cocatalyst Al(O i Pr) 3 with the oligostyrene macroinitiator in acetone, followed by precipitation.…”

Section: Resultsmentioning

confidence: 99%

Living radical emulsion polymerization using the nanoprecipitation technique: An extension to atom transfer radical polymerization

Chan‐Seng

Georges

2006

J. Polym. Sci. A Polym. Chem.

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Living radical polymerizations of styrene were performed under emulsion atom transfer radical polymerization conditions with latexes prepared by a nanoprecipitation technique recently developed for the stable free-radical polymerization process. Latexes were prepared by the precipitation of a solution of low-molecular-weight polystyrene in acetone into a solution of a surfactant in water. The resulting particles were swollen with styrene and then heated. The effects of various surfactants and hydrophobic ligands, the reaction temperature, and the ligand/copper(I) bromide ratio were studied. The best results were obtained with the nonionic surfactant Brij 98 in combination with the hydrophobic ligand N,N-bis(2-pyridylmethyl)octadecylamine and a ligand/copper(I) bromide ratio of 1.5 at a reaction temperature of 85-90 8C. Under these conditions, latexes with good colloidal stability with average particle diameters of 200 nm were obtained. The molecular weight distributions of the polystyrenes were narrow, although the experimental molecular weights were slightly larger than the theoretical ones because not all the macroinitiator appeared to reinitiate.

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Ruthenium-catalyzed isomerization of homoallylic alcohols in water

Cited by 41 publications

References 58 publications

Ruthenium‐Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols

Ruthenium‐Catalyzed Functionalization of Pyrroles and Indoles with Propargyl Alcohols

Microwave-assisted tandem allylation-isomerization reaction catalyzed by a mesostructured bifunctional catalyst in aqueous media

Living radical emulsion polymerization using the nanoprecipitation technique: An extension to atom transfer radical polymerization

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