- Palladium-catalyzed Michael addition of indoles to α,β- unsaturated ketones in an ionic liquid
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The PdCl2(CH3CN)2-catalyzed Michael addition reaction of indoles with α,β-unsaturated ketones in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim][BF4]) to afford the corresponding 3-alkylated i
- Li, Wei-Jun,Lin, Xu-Feng,Wang, Jun,Li, Guo-Liang,Wang, Yan-Guang
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- Air-stable μ2-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application
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Three air-stable zirconocene perfluoro-octanesulfonates were successfully synthesized by treatment of C8F17SO3Ag with (RCp)2ZrCl2 [R = H, n-Bu, t-Bu]. According to X-ray analysis, they have μ2-hydroxyl bridged cationic binuclear structures: (i) [CpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2THF·4H2O (1a·2THF·4H2O), (ii) [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·6H2O (2a·6H2O), and (iii) [t-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2C3H6O·8H2O (3a·2C3H6O·8H2O). The ligands of water and organic molecules in the complexes originated from the moist air and solvent during their recrystallization. These complexes were characterized with different techniques, and found to show water tolerance, air/thermal stability as well as strong Lewis acidity. Moreover, the complexes showed highly catalytic activity in various reactions of C–C bond formation. With good recyclability, they should find wide applications in organic chemistry.
- Zhang, Xiaohong,Xu, Xinhua,Li, Ningbo,Liang, Zhiwu,Tang, Zilong
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supporting information
p. 1926 - 1932
(2018/03/21)
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- Supported iron catalysts for Michael addition reactions
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Heterogeneous catalysts have been widely used for chemical transformations and offer easy product separation in addition to their high activity. Iron is an earth-abundant metal, but it has not been studied thoroughly as heterogeneous catalysts for organic
- Ye, Rong,Faucher, Franco F.,Somorjai, Gabor A.
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- Strong Lewis acids of air-stable binuclear triphenylantimony(V) complexes and their catalytic application in C-C bond-forming reactions
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Two air-stable novel Lewis acids of triphenylantimony(V) pentafluorbezenesulfonates (2) and perfluorooctanesulfonates (3) were successfully synthesized and characterized. X-ray studies and thermo-gravimetric analysis found that these complexes showed high anti-hydrolyzability and thermal stability. The high catalytic activity and excellent recyclability of these complexes were achieved in the Michael addition reaction and the allylation reaction. On account of their stability, storability, as well as catalytic efficiency, these complexes should find a broad range of utility in organic synthesis.
- Li, Ningbo,Qiu, Renhua,Zhang, Xiaohong,Chen, Yun,Yin, Shuang-Feng,Xu, Xinhua
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p. 4275 - 4281
(2015/06/08)
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- Highly effective and regioselective Michael addition of indoles to α,β-unsaturated ketones promoted by pentafluorophenylammonium triflate
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A simple, inexpensive, environmentally friendly and efficient route for Michael addition of indoles to α,β-unsaturated ketones using pentafluorophenylammonium triflate (PFPAT) as a catalyst is described. Various indole derivatives were synthesized in good
- Khaksar, Samad,Vahdat, Seyed Mohammad,Rezaee, Fatemeh
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p. 144 - 147
(2013/04/24)
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- Synthesis and structures of air-stable binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate and their catalytic application in C-C bond-forming reactions
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The two air-stable m2-hydroxy-bridged binuclear hafnocene perfluorobutanesulfonate and perfluorobenzenesulfonate complexes were successfully synthesized. The high catalytic activity and recyclability of these complexes were exemplified for various carbon-carbon bond formation reactions. Compared with our previously reported hafnocene perfluorooctanesulfonate, these complexes show stronger Lewis acidity and better catalytic activity, and should find broad applications in organic synthesis.
- Li, Ningbo,Zhang, Xiaohong,Xu, Xinhua,Chen, Yun,Qiu, Renhua,Chen, Jinyang,Wang, Xie,Yin, Shuang-Feng
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supporting information
p. 2430 - 2440
(2013/10/01)
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- D-camphor-10-sulfonic acid: A water compatible organocatalyst for Friedel-Crafts reaction of indoles with electron deficient olefins
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A recyclable natural product derived Bronsted acid (D-CSA) catalyzes the Friedel-Crafts addition of indole derivatives to nitroalkenes and enones in water at room temperature in good to excellent yields (71-98%).
- Chauhan, Pankaj,Singh, Sarbjit,Chimni, Swapandeep Singh
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p. 245 - 251
(2013/05/08)
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- High-pressure accelerated asymmetric organocatalytic friedel-crafts alkylation of indoles with enones: Application to quaternary stereogenic centers construction
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An organocatalytic Friedel-Crafts alkylation of indoles with α,β-unsaturated ketones was found to be efficiently accelerated under high-pressure conditions with a low loading of chiral primary amine salts with good yield and enantioselectivity up to 90%. This approach also allows, for the first time, selected indole derivatives containing quaternary stereogenic centers to be obtained from prochiral β,β-disubstituted enones with an enantioselectivity up to 80%.
- Lyzwa, Dawid,Dudzinski, Krzysztof,Kwiatkowski, Piotr
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supporting information; experimental part
p. 1540 - 1543
(2012/06/15)
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- Magnetic nanoparticle supported polyoxometalates (POMs) via non-covalent interaction: Reusable acid catalysts and catalyst supports for chiral amines
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Magnetic polyoxometalates (POMs) are obtained by a simple sonication between functionalized magnetic nanoparticles and polyoxometalates. This material can be used not only as a highly active acid catalyst, but also as a catalyst support for chiral amines.
- Zheng, Xiaoxi,Zhang, Long,Li, Jiuyuan,Luo, Sanzhong,Cheng, Jin-Pei
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supporting information; experimental part
p. 12325 - 12327
(2011/12/15)
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- Task-specific ionic-liquid-catalyzed efficient synthesis of indole derivatives under solvent-free conditions
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A sulfonic-acid-functionalized ionic liquid is used as a Bronsted acid catalyst for the efficient synthesis of indole derivatives in good-to-high yields at room temperature under solvent-free conditions. The catalyst can be reused for ten consecutive runs without significant loss of activity.
- Das, Sudarshan,Rahman, Matiur,Kundu, Dhiman,Majee, Adinath,Hajra, Alakananda
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experimental part
p. 150 - 154
(2010/04/03)
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- Enantioselective friedel-crafts alkylation of furans and indoles with simple α,β-Unsaturated ketones catalyzed by oxazaborolidinone
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allo-Threonine-derived oxazaborolidinone (OXB) catalyzes the Friedel-Crafts alkylation of furans and indoles with simple acyclic α,β-unsaturated ketones to give the products in high yields and with high enantioselectivities. With 5-10 mol% of the OXB cata
- Adachi, Shinya,Tanaka, Fumi,Watanabe, Kazuya,Watada, Atsushi,Harada, Toshiro
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experimental part
p. 2652 - 2669
(2010/09/08)
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- Zirconium tetrakis(dodecylsulfate) as an efficient and recyclable lewis acid-surfactant-combined catalyzed C-C and C-N bond forming under mild and environmentally benign conditions
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A green catalytic method for C-C and C-N bond forming via Michael addition of aromatic amines and indoles to electron-deficient olefins using Zirconium tetrakis(dodecylsulfate) in water under mild conditions with high yields and selectivity has been developed. The reusability of the catalyst has been successfully examined without any noticeable loss of its catalytic activity.
- Jafarpour, Maasoumeh,Rezaeifard, Abdolreza,Aliabadi, Marzieh
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scheme or table
p. 94 - 99
(2010/04/23)
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- Hf(Otf)4-catalyzed 1,4-addition reactions of indole to enone in the presence of meso and chiral pyridine-diamine ligands
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Hf(OTf)4-catalyzed 1,4-addition reactions of indole to enones in the presence of pyridinediamine are described. Although a dimer and a trimer of indole were produced under the Hf(OTf)4 catalyzed reaction conditions of indole, the add
- Aburatani, Sachiko,Uenishi, Jun'ichi
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experimental part
p. 1407 - 1416
(2009/04/04)
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- Synthesis of 3-substituted indoles promoted by pulverization-activation method catalyzed by Bi(NO3)3·5H2O
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(Chemical Equation Presented) A new, facile, efficient, "green" and chemoselective procedure for the synthesis of indole derivatives has been developed with pulverization-activation method catalyzed by Bi(NO 3)3·5H2O (PAMC- Bi(NO3) 3·5H2O) through grinding of indoles with aldehydes or Michael acceptors in the presence of catalytic amounts of Bi(NO 3)3·5H2O under solvent-free conditions.
- Khodaei, Mohammad M.,Mohammadpoor-Baltork, Iraj,Memarian, Hamid R.,Khosropour, Ahmad R.,Nikoofar, Kobra,Ghanbary, Parvin
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p. 377 - 381
(2008/09/20)
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- Sustainable conjugate addition of indoles catalyzed by acidic ionic liquid immobilized on silica
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A new protocol for 1,4-conjugate addition of indoles to vinyl ketones has been developed, employing Lewis acidic ionic liquid immobilized on silica, ILIS-SO2Cl, as a catalyst, which exhibited an efficient, mild and recyclable nature. The reacti
- Hagiwara, Hisahiro,Sekifuji, Masayoshi,Hoshi, Takashi,Suzuki, Toshio,Quanxi, Bao,Qiao, Kun,Yokoyama, Chiaki
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p. 608 - 610
(2008/12/22)
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- 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2,2,2]octane bis(tetrafluoroborate) as novel and efficient reagent for the conjugate addition of indoles to α,β-unsaturated ketones
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Indoles undergo smooth conjugate addition with α,β-unsaturated ketones in the presence of 10 mol % Selectfluor under extremely mild conditions to afford the corresponding Michael adducts in high to quantitative yields with 1,4-selectivity. Copyright
- Yadav,Reddy, B. V. Subba,Raju,Ravindar,Baishya, Gakul
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p. 1056 - 1057
(2008/02/10)
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- Triflic acid-catalyzed Michael reactions of indole and pyrrole compounds with α,β-unsaturated ketones in water
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The Michael reactions of indole and pyrrole compounds to α,β-unsaturated ketones catalyzed by triflic acid (HOTf, 0.1-1 mol%) were performed in water to give alkylated indoles (3a-m) and dialkylsubstituted pyrroles (6a-b) in good to excellent yields. Copy
- Zhang, Hai-Bo,Liu, Li,Liu, Yu-Liang,Chen, Yong-Jun,Wang, Jun,Wang, Dong
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p. 173 - 181
(2007/10/03)
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- Organocatalytic C3-selective Friedel-Crafts alkylations of indoles with α,β-unsaturated ketones
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The use of an equimolar amount of pyrrolidine and HClO4 (30 mol%) was found to be effective in promoting the conjugate addition of indoles to (E)-α,β-unsaturated ketones, affording the corresponding β-indolyl ketones in excellent yields. The Ro
- Li, Dong-Ping,Guo, Ying-Cen,Ding, Yu,Xiao, Wen-Jing
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p. 799 - 801
(2008/02/03)
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- Efficient michael addition of indoles using bismuthyl perchlorate as catalyst
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An efficient method for Michael addition of indoles hasbeen developed using bismuthyl perchlorate (BiOClO4·xH2O) as catalyst. The reaction proceeds to give 3-substituted indoles excellently stirring indoles and Michael acceptors in acetonitrile in the presence of the catalyst at room temperature or in much shorter reaction times under sonication at ambient temperature.{A figure is presented}.
- Mohammadpoor-Baltork, Iraj,Reza Memarian, Hamid,Reza Khosropour, Ahmad,Nikoofar, Kobra
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p. 1837 - 1843
(2007/10/03)
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- Conjugate addition of indoles to α,β-unsaturated ketones using Cu(OTf)2 immobilized in ionic liquids
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Indoles undergo smooth conjugate addition with α,β-unsaturated ketones in the presence of 10 mol% copper(II) triflate immobilized in air and moisture stable [bmim]BF4 ionic liquid under mild conditions to afford the corresponding conjugate addi
- Yadav,Reddy,Baishya, Gakul,Reddy,Narsaiah
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p. 9541 - 9544
(2007/10/03)
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- The ultra high pressure conjugate addition of indoles to electron- deficient olefins
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The addition of indole and methyl indole at both high and ambient pressures to a series of Michael acceptors under the influence of ytterbium triflate was investigated. Under ambient pressure the more reactive and less sterically hindered electrophiles ga
- Harrington, Paul,Kerr, Michael A.
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p. 1256 - 1265
(2007/10/03)
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