- "Counter" Phase Transfer Catalysis by Water-soluble Phosphine Complexes. Catalytic Reduction of Allyl Chlorides and Acetates with Sodium Formate in Two-phase Systems
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In the reduction of allyl chlorides and acetates with sodium formate in a heptane-water two-phase system, water-soluble palladium complexes function as a novel type of catalyst which transports the substrate into the aqueous phase and causes it to react with sodium formate.
- Okano, Tamon,Moriyama, Yoshiyuki,Konishi, Hisatoshi,Kiji, Jitsuo
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Read Online
- Hemin Catalyzed Dealkylative Intercepted [2, 3]-Sigmatropic Rearrangement Reactions of Sulfonium Ylides with 2, 2, 2-Trifluorodiazoethane
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A dealkylative intercepted [2, 3]-sigmatropic rearrangement reaction of allylic sulfides with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is reported, the commercially available and biocompatible catalyst hemin was found to efficiently catalyze this transformation across a diverse set of allylic sulfides with in situ generated CF3CHN2, providing excellent yields (up to 99%) under mild condition without inert gas protection. In addition, CF3CHN2 exhibited unique reactivity toward this process compared with other frequently used diazo reagents. This work expands the range of carbene-mediated transformations catalyzed by hemin and introduces a concise and general strategy for exploiting new possibility of reactions concerning organosulfides. (Figure presented.).
- Yan, Xiaojing,Li, Chang,Xu, Xiaofei,Zhao, Xiaoyong,Pan, Yuanjiang
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p. 2005 - 2011
(2020/05/18)
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- Efficient Enzymatic Preparation of Flavor Esters in Water
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A straightforward biocatalytic method for the enzymatic preparation of different flavor esters starting from primary alcohols (e.g., isoamyl, n-hexyl, geranyl, cinnamyl, 2-phenethyl, and benzyl alcohols) and naturally available ethyl esters (e.g., formate, acetate, propionate, and butyrate) was developed. The biotransformations are catalyzed by an acyltransferase from Mycobacterium smegmatis (MsAcT) and proceeded with excellent yields (80-97%) and short reaction times (30-120 min), even when high substrate concentrations (up to 0.5 M) were used. This enzymatic strategy represents an efficient alternative to the application of lipases in organic solvents and a significant improvement compared with already known methods in terms of reduced use of organic solvents, paving the way to sustainable and efficient preparation of natural flavoring agents.
- Perdomo, Igor Chiarelli,Gianolio, Stefania,Pinto, Andrea,Romano, Diego,Contente, Martina Letizia,Paradisi, Francesca,Molinari, Francesco
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p. 6517 - 6522
(2019/06/20)
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- Photocatalyzed ortho-Alkylation of Pyridine N-Oxides through Alkene Cleavage
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A photocatalyzed reaction of pyridine N-oxides with alkenes gives ortho-alkylated pyridines with cleavage of the carbon–carbon double bond. Benzyl and secondary alkyl groups are incorporated at the ortho position of pyridines in one pot.
- Zhou, Wang,Miura, Tomoya,Murakami, Masahiro
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supporting information
p. 5139 - 5142
(2018/05/30)
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- An Effective Pt-Cu/SiO2 Catalyst for the Selective Hydrogenation of Cinnamaldehyde
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The bimetal catalyst Pt-Cu/SiO2 was prepared by the impregnation method. Its catalytic performance was investigated by the selective hydrogenation of cinnamaldehyde. Pt-Cu/SiO2 exhibited much higher selectivity (64.1%) to cinnamyl al
- Wang, Dong,Zhu, Yujun
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- Lewis Base Promoted Reduction of CO2 with BH3NH3 into Boryl Formates: CO2 as a Carbon Source in Organic Synthesis Under Mild Conditions
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Lewis base promoted selective reduction of CO2 into boryl formates by using BH3NH3 as a reductant under mild conditions has been reported. The boryl formates, generated in situ, were shown to be reactive and versatile sources of formyl compounds to create new C–N, C–O, and C–C bonds. The reactivity of the boryl formates to yield formic acid, formamides, formates, secondary alcohols, and benzoheterocyclic rings was investigated.
- Zhang, Bo,Du, Gaixia,Hang, Wei,Wang, Sheng,Xi, Chanjuan
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supporting information
p. 1739 - 1743
(2018/04/24)
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- Application of polydopamine sulfamic acid-functionalized magnetic Fe3O4 nanoparticles (Fe3O4@PDA-SO3H) as a heterogeneous and recyclable nanocatalyst for the formylation of alcohols and amines under solvent-free conditions
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Herein, formylation of structurally different amines and alcohols with ethyl formate was carried out in the presence of a catalytic proportion of sulfonic acid supported on polydopamine (PDA)-encapsulated Fe3O4 nanoparticles as a heterogeneous, recyclable, and greatly efficient catalyst; this method provided the corresponding N-formyl compounds in good to excellent yields under solvent-free conditions. The magnetically catalytic system was recovered, by-passing the time-consuming filtration operation using an external magnet device. This procedure also increases the purity of the product and promises economic and ecological advantages. Furthermore, the recovery and reuse of the catalyst was demonstrated five times without detectable loss in the activity.
- Taheri, Sepideh,Veisi, Hojat,Hekmati, Malak
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p. 5075 - 5081
(2017/07/11)
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- N-Heterocyclic Carbene Catalyzed Transformylation
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The N-heterocyclic carbene (NHC) catalyzed transformylation has been developed for the conversion of 1°, 2°, and 3° alcohols to the corresponding formates. The reaction employs low catalyst loadings and methyl formate as the formyl transfer reagent. The scope of the reaction is broad with 23 examples reported with good yields (59-96%). The reaction is insensitive to common nitrogen and oxygen protecting groups and can be achieved in the presence of a number of heterocycles.
- Fernando, Jared E. M.,Levens, Alison,Moock, Daniel,Lupton, David W.
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p. 3505 - 3510
(2017/07/27)
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- Selective hydrogenation of cinnamaldehyde to cinnamal alcohol over platinum/graphene catalysts
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Catalysts made of Pt nanoparticles dispersed on graphene (X wt%Pt/G, X=2.0, 3.5, and 5.0) were prepared and characterized by XRD, Raman spectroscopy, BET surface area measurements, TEM, and X-ray photoelectron spectroscopy (XPS), and a 3.5 wt% Pt supported on Vulcan Carbon catalyst (3.5 wt%Pt/VC) was included as a reference. Although the mean Pt nanoparticle size is approximately 4.4 nm for all X wt%Pt/G and 3.5 wt%Pt/VC catalysts, cinnamal alcohol was produced with high selectivity only with the graphene-supported catalysts: 92% conversion and 88% selectivity toward cinnamal alcohol were obtained with 3.5 wt%Pt/G. This catalyst also showed good stability in recycling tests. The good selectivity observed with the graphene-based catalysts is attributed to the higher fraction of reduced surface Pt0 atoms seen on the surface of the Pt nanoparticles (determined by XPS). This interpretation is consistent with DFT calculations. Additional π -π interactions between cinnamaldehyde and graphene may also play a role in the selective hydrogenation of cinnamaldehyde.
- Ji, Xiwang,Niu, Xiaoyu,Li, Bo,Han, Qing,Yuan, Fulong,Zaera, Francisco,Zhu, Yujun,Fu, Honggang
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p. 3246 - 3253
(2015/02/18)
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- Formylation of alcohol with formic acid under solvent-free and neutral conditions catalyzed by free I2 or I2 generated in situ from Fe(NO3)3·9H2O/NaI
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Different alcohols were formylated by formic acid under solvent-free conditions in the presence of iodine as the catalyst with good-to-high yields at room temperature. I2 generated in situ from Fe(NO3) 3·9H2O/NaI also catalyzed the formylation of the alcohols under solvent-free conditions. This gives a green and efficient reaction at room temperature, in which the use of toxic and corrosive molecular I2 is avoided.
- Amin, Rostami,Ardeshir, Khazaei,Heidar Ali, Alavi-Nik,Zahra, Toodeh-Roosta
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experimental part
p. 60 - 64
(2011/10/08)
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- Efficient one-step conversion of tetrahydropyranyl ethers into acetates and formates in the presence of potassium dodecatungstocobaltate K 5CoW12O40·3H2O
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Tetrahydropyranyl ethers derived from primary alcohols were directly and efficiently converted into the corresponding acetates and formates by the action of ethyl acetate, acetic acid, acetic anhydride, and ethyl formate in the presence of a catalytic amount of potassium dodecatungstocobaltate K 5CoW12O40 ? 3H2O. Tetrahydropyranyl ethers derived from secondary alcohols and phenols can also be transformed into the corresponding acetates with the use of acetic anhydride, but K5CoW12O40 ? 3H2O was ineffective for esterification with ethyl acetate, acetic acid, and ethyl formate.
- Rafiee,Tangestaninejad,Habibi,Mohammadpoor-Baltork,Mirkhani
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p. 393 - 395
(2007/10/03)
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- Acetylation and formylation of alcohols in the presence of silica sulfuric acid
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Alcohols are converted to esters in a mild, clean, and efficient reaction with acetic and formic acids in the presence of silica sulfuric acid. All reactions were performed under mild and completely heterogeneous conditions in refluxing n-hexane.
- Shirini, Farhad,Zolfigol, Mohammad Ali,Mohammadi, Kamal
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p. 1617 - 1621
(2007/10/03)
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- Selective formylation of alcohols in the presence of phenols with chloral
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Primary and secondary alcohols were formylated selectively in the presence of phenols by stirring with chloral in acetone over anhydrous K2CO3 at ambient temperatures in high yields.
- Ram, Ram N,Meher, Nabin Kumar
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p. 2997 - 3001
(2007/10/03)
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- Novel catalytic acetylation and formylation of alcohols with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O)
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Acetylation and formylation reactions of alcohols with ethyl acetate, acetic acid and ethyl formate were catalyzed with potassium dodecatungstocobaltate trihydrate (K5CoW12O40·3H2O) in a mild, efficient and convenient method with high to excellent yields.
- Habibi, Mohammad H,Tangestaninejad, Shahram,Mirkhani, Valiollah,Yadollahi, Bahram
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p. 8333 - 8337
(2007/10/03)
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- Catalytic esterification of alcohols, carboxylic acids and transesterification reactions with cerium(IV) triflate
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Esterification reactions of alcohols with acetic, chloroacetic, trifluoroacetic, propionic, stearic, and benzoic acids were catalyzed with Ce(OTf)4 in a solvent or under solvent-free conditions with high yields. The formylation and acetylation of primary and secondary alcohols were also easily achieved in ethyl formate and ethyl acetate. A high retention of the configuration was observed in the acetylation and formylation of (-)-menthol.
- Iranpoor, Nasser,Shekarriz, Marzieh
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p. 455 - 458
(2007/10/03)
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- Conversion of trimethylsilyl ethers to acetyl or formyl esters with TiCl4
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A simple method is described for the efficient conversion of trimethylsilyl ethers to their corresponding acetyl and formyl esters in refluxing ethyl acetate or ethyl formate in the presence of TiCl4.
- Iranpoor, Nasser,Zeynizadeh, Behzad
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p. 2123 - 2128
(2007/10/03)
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- Conversion of alkyl halides into the corresponding alcohols under mild reaction conditions
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Reaction of primary, cyclopentyl, allyl and arylmethyl halides, but not an acyclic secondary halide or a tertiary halide, in acetone or tetrahydrofuran with the formate form of a commercial anion exchange resin gave formate esters in good yields. The formates were hydrolysed efficiently to the corresponding alcohols by a brief treatment with hydrochloric acid. Reaction of primary alkyl bromides or iodides, secondary alkyl bromides, cinnamyl and arylmethyl halides in tetrahydropyran or 1,4-dioxane with the bicarbonate form of the same anion-exchange resin gave the corresponding alcohols directly in good yields. This latter reaction can be carried out successfully in the presence of ester or amide groups.
- Ruddick, Clare L.,Hodge, Philip,Houghton, Mark P.
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p. 1359 - 1362
(2007/10/03)
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