- A novel synthesis of allyl sulfides in aqueous media promoted by indium
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Allyl bromides react smoothly with sodium alkyl thiosulfates promoted by indium in aqueous media to give allyl sulfides in moderate to good yields.
- Zhan, Zhuangping,Zhang, Yongmin
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- Aqueous hemin catalyzed sulfonium ylide formation and subsequent [2,3]-sigmatropic rearrangements
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A mild hemin catalytic system for sulfonium ylide generation via a metal carbenoid and a subsequent [2,3]-sigmatropic rearrangement reaction in aqueous solvent is well-established, with the assistance of cyclodextrin (CD) and Triton X-100. The protocol displays high catalytic activity with a broad substrate scope of aryl/alkyl allyl sulfides and diazo reagents, affording homoallyl sulfide products in up to 99% yield. Notably, this catalytic system is successful for water-insoluble allyl sulfides but ineffective for allyl amines or allyl ethers. Moreover, an unprecedented cascade reaction of sulfonium ylide formation, [2,3]-sigmatropic rearrangement and C-H insertion was reported.
- Xu, Xiaofei,Li, Chang,Tao, Zhihao,Pan, Yuanjiang
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supporting information
p. 1245 - 1249
(2017/08/15)
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- Scope of the allylation reaction with [RuCp(PP)]+ catalysts: Changing the nucleophile or allylic alcohol
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The scope of the dehydrative allylation reaction using allyl alcohol as allyl donor with [RuCp(PP)]+ complexes as catalysts is explored. Aliphatic alcohols are successfully allylated with allyl alcohol or diallyl ether, obtaining high selectivity for the alkyl allyl ether. The reactivity of aliphatic alcohols is in the order of primary > secondary tertiary. The tertiary alcohol 1-adamantanol reacts extremely slowly in the absence of strong acid, but when HOTs is added, reasonable yields of 1-adamantyl allyl ether are obtained. The alkyl allyl ether is found to be the thermodynamically favored product over diallyl ether. Apart from alcohols, thiols and indole are also efficiently allylated, while aniline acts as a catalyst inhibitor. Allylation reactions with various substituted allylic alcohols give products with retention of the substitution pattern. It is proposed that a Ru(IV) σ-allyl species plays a key role in the mechanism of these allylation reactions.
- Van Rijn, Jimmy A.,Guijt, Marieke C.,De Vries, Dwight,Bouwman, Elisabeth,Drent, Eite
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experimental part
p. 212 - 219
(2012/04/17)
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- Allylation of Alcohols and Carboxylic Acids with Allyl Acetate Catalyzed by [Ir(cod)2]+BF4- Complex
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A facile method for the synthesis of allyl alkyl ethers from alcohols with allyl acetate was developed by the use of [Ir(cod)2] +BF4- complex. For instance, the reaction of allyl acetate with n-octyl alcohol in the presence of a catalytic amount of [Ir(cod)2]+BF4- complex afforded allyl octyl ether in quantitative yield. Allyl carboxylates were also prepared by the exchange reaction between carboxylic acids and allyl acetate in good yields. The [Ir(cod)2]+BF4- complex catalyzed the reaction of alkyl and aromatic amines with allyl acetate to lead to the corresponding allylamines in fair to good yields.
- Nakagawa, Hideto,Hirabayashi, Tomotaka,Sakaguchi, Satoshi,Ishii, Yasutaka
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p. 3474 - 3477
(2007/10/03)
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- Process for producing allyl-containing compounds
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An allyl-containing compound represented by following Formula (3): wherein R2, R3, R4, R5 and R6 may be the same as or different from one another and each represent hydrogen atom or an organic group; R7 represents an organic group; and Y represents oxygen atom or sulfur atom, is produced by reacting an allyl ester compound represented by following Formula (1): wherein R1 represents hydrogen atom or an organic group; and R2, R3, R4, R5 and R6 are as defined above, with a compound represented by following Formula (2):R7-Y-H wherein R7 is an organic group; and Y is as defined above, in the presence of at least one transition element compound.
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- A novel method for the synthesis of allylic sulfides from disulfides and allylytterbium bromide
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In presence of trace of methyl iodide (Mel), allylytterbium bromide is formed by the reaction of metallic ytterbium and allylic bromide, which reacts with disulfides to give the corresponding allylic sulfides in good yields under mild and neutral conditions.
- Su,Li,Zhang,Li
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p. 263 - 264
(2007/10/03)
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- A Novel Synthesis of Allyl Sulfides by Organosamarium Reagents
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Organosamarium reagents react with sodium alkyl thiosulfates to afford allyl Sulfides; a reaction mechanism involving organosamarium(II) and Organosamarium (III) intermediates is suggested.
- Zhan, Zhuangping,Zhang, Yongmin
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p. 148 - 149
(2007/10/03)
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- The synthesis of allyl sulfides by organosamarium reagent
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Organosamarium reagent reacts with disulfides to afford allyl sulfides in THF.
- Yu, Mingxin,Zhang, Yongmin
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p. 2743 - 2748
(2007/10/03)
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- Low pressure hydrogenation of unsaturated sulphides with homogeneous and heterogeneous ruthenium catalysts
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Ru2O·nH2O and [Ru3O(AcO)6(H2O)3]+AcO- were examined for catalytic activity in the hydrogenation of a series of unsaturated sulphides under heterogeneous and homogeneous conditions, respectively. By the appropriate combination of these two methodologies, a number of saturated sulphides could be synthesized in satisfactory to good yields, thus minimizing side reactions.
- Cere, Vanda,Massaccesi, Franco,Pollicino, Salvatore,Ricci, Alfredo
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p. 899 - 907
(2007/10/03)
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