- Friedel-crafts alkylation of arenes catalyzed by ion-exchange resin nanoparticles: An expedient synthesis of triarylmethanes
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Friedel-Crafts alkylation of electron-rich arenes with aldehydes has been achieved in the presence of an active and selective Amberlyst-15 catalyst at the reaction temperature of 60 ° C in solvent-free conditions. The catalyst exhibitsby a very high activity and offers the corresponding triarylmethanes in excellent yields with a high selectivity. The use of highly reactive and selective Amberlyist-15 makes this procedure simple, convenient, cost-effective, practical and environmentally friendly. This method provides an easy access to triarylmethanes in a single step using a readily available acidic ionic resin, which is a stable and easy to separate from the reaction mixture by a simple filtration technique.
- Reddy, B. V. Subba,Venkateswarlu,Sridevi,Aldeyab, Salem S.,Vinu, Ajayan
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p. 6826 - 6832
(2015/11/24)
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- A rapid, highly efficient, and general protocol for the synthesis of functionalized triarylmethanes: A straightforward access for the synthesis of (-)-tatarinoid C
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A rapid, efficient, and convenient synthesis of functionalized triarylmethane is described by the Friedel-Crafts alkylation of methoxybenzenes with a variety of aldehydes in the presence of BF3·OEt 2. The generality of the method is demonstrated by screening a variety of di- or tri-substituted arenes as well as substituted aromatic, heteroaromatic, and aliphatic aldehydes. (-)-Tatarinoid C is synthesized in a single step following the same protocol.
- Babu, B. Madhu,Thakur, Pramod B.,Nageswara Rao,Santosh Kumar,Meshram
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p. 1868 - 1872
(2014/03/21)
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- Br?nsted acid ionic liquids catalyzed Friedel-Crafts Alkylations of electron-rich arenes with aldehydes
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Triarylmethanes (TRAMs) and diarylalkanes (DIAAs) are valuable intermediates with wide applications in many fields. TRAMs are usually obtained from the acid-catalysed bisarylation of activated aryl aldehydes. However, the synthesis poses many problems, such as harsh reaction conditions, and the disposal of the excess solvents and/or toxic metal waste. In this study, some functionalized ionic liquids including Br?nsted acid ionic liquids (BAILs) and traditional ionic liquids were designed and synthesized. BAILs catalyzed Friedel-Crafts (F-C) alkylation was applied in this specific reaction for the first time. And the BAILs showed bifunctional properties acting as catalyst and solvent. Research shows that BAILs can be used for catalyzing F-C alkylations of electron-rich arenes with aromatic or aliphatic aldehydes successfully under mild reaction conditions. Furthermore, BAILs containing triflic anion has higher activity than other BAILs and traditional ionic liquids. [HSO 3-pmim][OTf] gets the highest yields in the presence of 20 mol% of BAILs at 40 °C to give the corresponding TRAMs derivatives. After five cycles, the yields remain about 93-97%. Finally, according to IR spectrum and the experimental validation, the aromatic electrophilic substitution reaction was considered to be the possible catalysis mechanisms.
- Wang, Ailing,Zheng, Xueliang,Zhao, Zhuangzhi,Li, Changping,Cui, Yingna,Zheng, Xuefang,Yin, Jingmei,Yang, Guang
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p. 198 - 204
(2014/07/08)
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- Room-temperature bismuth-catalyzed bis-arylation of carbonyl compounds with aryl ethers and phenols
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Using Bi2(SO4)3 as the catalyst and TMSCl as the additive, a wide variety of aldehydes, ketones, and acetals were smoothly condensed with aryl ethers at room temperature to provide the corresponding diarylmethanes and triarylmethanes selectively in good to excellent yields. Using Bi2(SO4)3 as the catalyst and TMSCl as the additive, a wide variety of aldehydes, ketones, and acetals were smoothly condensed with aryl ethers at room temperature to selectively provide the corresponding diarylmethanes and triarylmethanes in good to excellent yields. Copyright
- Liu, Congrong,Li, Manbo
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p. 1274 - 1278
(2013/11/06)
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- H3PW12O40-catalysed alkylation of arenes and diveratrylmethanes: Convenient routes to triarylmethanes and to symmetrical and unsymmetrical 9,10-diaryl-2,3,6,7-tetramethoxyanthracenes
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An efficient method for the synthesis of triarylmethanes and difurylarylmethanes through solventless reactions between aldehydes and arenes in the presence of H3PW12O40 as a reusable catalyst under thermal and microwave irradiation conditions has been developed. H3PW12O40-catalysed one-pot consecutive Friedel-Crafts reactions between veratrole and aldehydes were also applied as a convenient protocol for the preparation of symmetrical 9,10-diaryl-2,3,6,7- tetramethoxyanthracenes.
- Mohammadpoor-Baltork, Iraj,Moghadam, Majid,Tangestaninejad, Shahram,Mirkhani, Valiollah,Mohammadiannejad-Abbasabadi, Kazem,Khavasi, Hamid R.
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experimental part
p. 1357 - 1366
(2011/04/17)
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- Facile and green synthesis of triarylmethanes using silica sulfuric acid as a reusable catalyst under solvent-free conditions
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A facile and environmentally-benign protocol has been developed for the synthesis of triarylmethanes (TAMs) from the reaction of different arenes and aldehydes in the presence of silica sulfuric acid (SSA) as a heterogeneous and reusable catalyst under solvent-free conditions. Easy work-up, short reaction times, high yields, high selectivity, mild and green conditions are other salient features of this method.
- Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Mohammadiannejad-Abbasabadi,Zolfigol
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experimental part
p. 934 - 943
(2012/04/17)
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- Ultrasound-assisted eco-friendly synthesis of triarylmethanes catalyzed by silica sulfuric acid
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An efficient and eco-friendly synthesis of triarylmethanes by the reaction of arenes with aldehydes in the presence of silica sulfuric acid as a heterogeneous and reusable catalyst under ultrasonic irradiation is reported. The advantages of this protocol are the use of green solvents, inexpensive catalyst, commercially available precursors, reusability of SSA, simple work-up, high yields and short reaction times.
- Mohammadpoor-Baltork,Moghadam,Tangestaninejad,Mirkhani,Mohammadiannejad-Abbasabadi,Zolfigol
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experimental part
p. 840 - 850
(2012/07/03)
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- FeCl3: an efficient catalyst for reactions of electron-rich arenes with imines or aziridines
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Iron(III) chloride was discovered highly effective as catalyst in the Friedel-Crafts reactions of electron-rich arenes with imines or aziridines. It was found that reactions of imines were highly substrate-dependent, which generated mono- or double-additi
- Wang, Zhiyong,Sun, Xiaoyu,Wu, Jie
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p. 5013 - 5018
(2008/09/21)
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- Catalytic selective bis-arylation of imines with anisole, phenol, thioanisole and analogues
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The first highly efficient double Friedel-Crafts reaction of N-tosyl imines with anisole, phenol, thioanisole and analogues has been developed to produce the corresponding symmetric diarylmethanes and triarylmethanes with high regioselectivity in the presence of a catalytic amount of Bi2(SO 4)3-TMSCl at room temperature. The Royal Society of Chemistry.
- Liu, Cong-Rong,Li, Man-Bo,Yang, Cui-Feng,Tian, Shi-Kai
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p. 1249 - 1251
(2008/12/21)
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- Convenient synthesis of triarylmethanes and 9,10-diarylanthracenes by alkylation of arenes with aromatic aldehydes using acetyl bromide and ZnBr2/SiO2
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Reaction of electron-rich arenes with acetyl bromide and aldehydes in the presence of silica gel-supported zinc bromide was carried out in benzene to give selectively the corresponding triarylmethanes or 9,10-diarylanthracenes in high yields depending upon the ratio of an arene and an aldehyde. The mild conditions employed are especially noteworthy.
- Kodomari, Mitsuo,Nagamatsu, Maki,Akaike, Megumi,Aoyama, Tadashi
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p. 2537 - 2540
(2008/09/21)
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- Br?nsted- and Lewis acid-catalyzed cyclization giving rise to substituted anthracenes and acridines
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A versatile acid-catalyzed method for the preparation of symmetrically and unsymmetrically substituted 9,10-diphenylanthracenes is explored. Diveratrylmethanes are prepared and converted into 10-phenylanthracene-9-carbaldehydes by Lewis acid catalysis and into 9-phenylacridines by reduction.
- Goossens, Raf,Smet, Mario,Dehaen, Wim
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p. 6605 - 6608
(2007/10/03)
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- ECHANGE DE SUBSTITUANTS EN SERIE ANTHRACENIQUE PAR CYCLO-ADDITIONS SUIVIES D'ELIMINATIONS SPONTANEES; APPLICATION A LA SYNTHESE D'UN CAPTEUR HYDROSOLUBLE D'OXYGENE SINGULET
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Condensation of benzaldehyde with veratrole in acidic media affords a one-pot synthesis of 2,3,6,7-tetramethoxy-9,10-diphenylanthracene 1f.The reaction of 1f with dimethyl acetylenedicarboxylate does not yield the expected adduct but leads directly to the tetramethyl 9,10-diphenylanthracene-2,3,6,7-tetracarboxylate 9b and other products, through successive cyclo-additions followed by spontaneous eliminations of dimethoxyacetylene or methoxycarbyne.
- Aubry, J. M.,Schmitz, C.,Rigaudy, J.,Cuong, Nguyen Kim
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p. 623 - 628
(2007/10/02)
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