727401-19-6Relevant articles and documents
Monoallylation and benzylation of dicarbonyl compounds with alcohols catalysed by a cationic cobalt(iii) compound
Chandra Sau, Mohan,Mandal, Smita,Bhattacharjee, Manish
, p. 9235 - 9245 (2021/03/16)
Monoallylation and monoalkylation of diketones and β-keto esters with allylic and benzylic alcohols catalysed by [Cp*Co(CH3CN)3][SbF6]2(I) are reported. The method does not require any additive and affords regioselective products. The mechanistic investigations were done byin situ1H NMR spectroscopy as well as control experiments. It has been shown that reactions proceedviaη3-allyl complex formation or ally ether intermediate. The alkylation takes placeviaonly ether intermediate. The resulting allylated and alkylated products have been used for the synthesis of eleven new trisubstituted pyrazoles and one pyrazolone.
Graphene oxide catalyzed ketone α-alkylation with alkenes: Enhancement of graphene oxide activity by hydrogen bonding
Meng, Guangrong,Patel, Mehulkumar,Luo, Feixiang,Li, Qingdong,Flach, Carol,Mendelsohn, Richard,Garfunkel, Eric,He, Huixin,Szostak, Michal
supporting information, p. 5379 - 5382 (2019/05/10)
Direct α-alkylation of carbonyl compounds represents a fundamental bond forming transformation in organic synthesis. We report the first ketone-alkylation using olefins and alcohols as simple alkylating agents catalyzed by graphene oxide. Extensive studies of the graphene surface suggest a pathway involving dual activation of both coupling partners. Notably, we show that polar functional groups have a stabilizing effect on the GO surface, which results in a net enhancement of the catalytic activity. The method represents the first alkylation of carbonyl compounds using graphenes, which opens the door for the development of an array of protocols for ketone functionalization employing common carbonyl building blocks and readily available graphenes.
Base-free benzylation of 1,3-dicarbonyl compounds using sulfamic acid supported on silica by linker: a combined experimental and theoretical approach
Karimzadeh, Morteza,Saberi Asl, Hamed,Hashemi, Hajar,Saberi, Dariush,Niknam, Khodabakhsh
, p. 2237 - 2244 (2018/10/31)
Abstract: Sulfamic acid stabilized on the surface of silica by the n-propyl organic group linker which is named silica-bonded N-propylsulfamic acid was applied as an efficient heterogeneous catalyst with good recyclability and reusability for direct benzylation of 1,3-dicarbonyl compounds using secondary aromatic alcohols or styrenes as alkylating agents in high yields and short reaction times. All the reactions were carried out in nitromethane as solvent under an air atmosphere. The catalyst showed reusable feature by six times without a significant loss in its activity. Graphical abstract: [Figure not available: see fulltext.].
Intra- and intermolecular alkylation of N, O-acetals and π-activated alcohols catalyzed by in situ generated acid
Hamon, Melanie,Dickinson, Niall,Devineau, Alice,Bolien, David,Tranchant, Marie-Jose,Taillier, Catherine,Jabin, Ivan,Harrowven, David C.,Whitby, Richard J.,Ganesan,Dalla, Vincent
, p. 1900 - 1912 (2014/04/03)
Intramolecular and intermolecular alkylations of carbocation precursors of limited ionization ability, principally N,O-acetals, without the use of an exogenous reagent have been developed. The reactions are carried out in 1,1,2,2-tetrachloroethane (TCE) a
Yb(OTf)3-promoted effective benzylation and allylation with N-tosyl amino group as a stable leaving group
Liu, Jinqian,Wang, Limin,Zheng, Xingzhou,Wang, Aili,Zhu, Mengyun,Yu, Jianjun,Shen, Qiang
supporting information; experimental part, p. 1843 - 1846 (2012/04/23)
A simple, inexpensive, environmentally friendly, and highly efficient benzylation and allylation of 1,3-dicarbonyl compounds with sulfonamides in the presence of Yb(OTf)3 is described. Yb(OTf)3 was proved to be a good catalyst for the cleavage of sp3 carbon-nitrogen bond. Various 1,3-dicarbonyl compounds can couple with a broad range of tosyl-activated benzylic and allylic amines to give diversely functionalized products in good to excellent yields.
Ruthenium salophen triflate: A reusable catalyst for alkylation of 1,3-dicarbonyl compounds
Barati, Behjat,Moghadam, Majid,Rahmati, Abbas,Mirkhani, Valiollah,Tangestaninejad, Shahram,Mohammadpoor-Baltork, Iraj
, p. 122 - 126 (2013/01/15)
Reaction of 1,3-dicarbonyl compounds with alcohols or olefins in the presence of catalytic amounts of electron-deficient [Ru(salophen)OTf] produced α-alkylated 1,3-dicarbonyls under solvent-free conditions. Different substituted benzylic alcohols were efficiently reacted with 2,4-pentanedione or 1,3-diphenyl-1,3-propanedione and their corresponding alkylated diones were obtained in good to excellent yield. On the other hand, substituted styrenes were also converted to their corresponding α-alkylated 1,3-dicarbonyls in good yields. The effect of reaction parameters such as solvent, amount of catalyst and axial substituent on the ruthenium salophen was also investigated. The catalyst was reusable several times without loss of its activity.
Magnesium bistrifluoromethanesulfonimide as an efficient catalyst for the hydroalkylation of aromatic olefins with 1,3-diketones under solvent-free conditions
Wang, Hong She,Zhao, Wei Xing
experimental part, p. 911 - 914 (2012/01/07)
An efficient magnesium bistrifluoromethanesulfonimide [Mg(NTf 2)2] catalyzed hydroalkylation of aromatic olefins with 1,3-diketones under solvent-free conditions has been developed. The reactions proceed smoothly to give the desired products in good yields in short reaction times.
Fe(ClO4)3·×H2O-Catalyzed direct C-C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles
Thirupathi, Ponnaboina,Kim, Sung Soo
experimental part, p. 2995 - 3003 (2010/06/14)
Fe(ClO4)3·×H2O as a highly effective catalyst for benzylation of 1,3-dikones, β-ketoesters, 1,3-diesters, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with various benzylic alcohols is described. The usefulness of this procedure is shown by a synthesis of bis-symmetrical triarylmethanes and one step synthesis of an anti-coagulant compound 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (Coumatetralyl (B)). The advantages of this protocol are broad scope, mild conditions, use of inexpensive catalyst and simplicity of operation since water is the only side product.
Triflic acid adsorbed on silica gel as an efficient and recyclable catalyst for the addition of β-dicarbonyl compounds to alcohols and alkenes
Liu, Pei Nian,Xia, Fei,Wang, Qing Wei,Ren, Yu Jie,Chen, Jun Qin
supporting information; experimental part, p. 1049 - 1055 (2010/08/04)
The silica gel supported triflic acid was readily prepared via simple absorption of TfOH onto chromatographic silica gel. This solid acid was applied as an efficient catalyst for the heterogeneous addition of various β-dicarbonyl compounds to a series of alcohols and alkenes, which afforded moderate to excellent yields under solvent-free conditions or in nitromethane. Moreover, this silica gel supported catalyst surprisingly exhibited higher reaction yields in comparison with the homogeneous catalyst and can be readily recovered and reused up to 6 times with almost maintained reactivity and yields.
Efficient nucleophilic substitution of -aryl alcohols with 1,3-dicarbonyl compounds catalyzed by tin ion-exchanged montmorillonite
Wang, Jiacheng,Masui, Yoichi,Onaka, Makoto
experimental part, p. 2493 - 2497 (2010/12/18)
Tin ion-exchanged montmorillonite demonstrated the high catalytic activity for the direct nucleophilic substitution of a hydroxyl group in -aryl alcohols with various 1,3-dicarbonyl compounds including less acidic 1,3-diesters in crude solvents to afford
