54921-86-7Relevant academic research and scientific papers
FeCl3·6H2O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
Chantana, Chayamon,Jaratjaroonphong, Jaray
, p. 2312 - 2327 (2021/02/09)
In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving group in the Csp3-Csp2 bond cleavage reaction. The operational ease, nonexpensive and environmentally friendly catalyst, mild reaction conditions, broad functional group tolerance, and scalability of this reaction strategy are advantages of the present procedure.
Niobium Pentachloride Mediated (Hetero)aromatic Aldehyde Friedel-Crafts Hydroxyalkylation with Arenes: An Efficient Strategy to Synthesize Triarylmethanes
Baviera, Giovanni S.,Donate, Paulo M.,Matias, Alexandre A.,Previdi, Daniel,Rodrigues, Shirley M. M.
, p. 4498 - 4506 (2019/11/21)
Niobium pentachloride is an efficient and useful Lewis acid to conduct Friedel-Crafts hydroxyalkylation between arenes and (hetero)aromatic aldehydes, to generate triarylmethanes. This practical methodology offers several advantages, such as short reaction time, mild experimental conditions, and excellent yields.
Synthesis method of triarylmethane and derivative thereof under solvent-free condition
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Paragraph 0041; 0042, (2018/02/28)
The invention discloses a synthesis method of triarylmethane and a derivative thereof under a solvent-free condition and belongs to the field of synthesis of organic compounds. According to the synthesis method disclosed by the invention, sulfamic acid is used as a catalyst and aromatic aldehyde and aromatic hydrocarbon are used as raw materials to synthesize a target object through one-step synthesis. The synthesis method disclosed by the invention has moderate reaction conditions, the catalyst is environmentally friendly and can be recycled and the yield is high; the low yield reaches 43 percent or more and the high yield reaches 98 percent or more; the synthesis method has relatively good universality, small influences on environment and actual popularization and application value.
Bi(OTf)3-Catalyzed One-Step Catalytic Synthesis of N-Boc or N-Cbz Protected α-Branched Amines
Jaratjaroonphong, Jaray,Tuengpanya, Surisa,Ruengsangtongkul, Sureeporn
, p. 559 - 567 (2015/08/11)
In this paper, N-Boc and N-Cbz protected α-branched amines are synthesized directly from commercially available aromatic/heteroaromatic compounds, aldehydes, and tert-butyl or benzyl carbamate bearing a variety of substituents. Bismuth(III) triflate is found to be a highly effective catalyst for this one-pot, three-component coupling reaction. In addition, the use of mild reaction conditions, low catalytic loading, easy removal of the N-protective group, and one-step synthesis under "open-flask" are advantages of the present procedure.
Br?nsted acid ionic liquids catalyzed Friedel-Crafts Alkylations of electron-rich arenes with aldehydes
Wang, Ailing,Zheng, Xueliang,Zhao, Zhuangzhi,Li, Changping,Cui, Yingna,Zheng, Xuefang,Yin, Jingmei,Yang, Guang
, p. 198 - 204 (2014/07/08)
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.
A rapid, highly efficient, and general protocol for the synthesis of functionalized triarylmethanes: A straightforward access for the synthesis of (-)-tatarinoid C
Babu, B. Madhu,Thakur, Pramod B.,Nageswara Rao,Santosh Kumar,Meshram
, p. 1868 - 1872 (2014/03/21)
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.
Iodine-catalyzed, one-pot, three-component aza-Friedel-Crafts reaction of electron-rich arenes with aldehyde/carbamate combinations
Jaratjaroonphong, Jaray,Krajangsri, Suppachai,Reutrakul, Vichai
experimental part, p. 2476 - 2479 (2012/06/01)
Iodine is shown to be an efficient catalyst for a one-step, three-component aza-Friedel-Crafts reaction of activated arenes or heteroarenes with benzyl or tert-butyl carbamates in combination with a wide variety of aldehydes in toluene under 'open-flask'
A new practical synthesis of triaryl and trisindolylmethanes under solvent-free reaction conditions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Magistris, Claudio,Venturello, Paolo
supporting information; experimental part, p. 8393 - 8399 (2012/04/04)
An efficient and practical synthesis of triaryl and trisindolylmethanes is reported via the bisarylation of aryl aldehydes with activated arenes. The new method features mild solvent-free reaction conditions, in most cases nearly stoichiometric reagent ra
Friedel-crafts arylation reactions of N -sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes catalyzed by FeCl 3·6H2O: Synthesis of triarylmethanes and bis-heteroarylarylmethanes
Thirupathi, Ponnaboina,Soo Kim, Sung
experimental part, p. 5240 - 5249 (2010/10/03)
(Figure presented) The FeCl3·6H2O-catalyzed Friedel-Crafts arylation reactions of N-sulfonyl aldimines or sulfonamidesulfones with electron-rich arenes and heteroarenes, which lead to the formation of triarylmethanes and bis-heteroar
Regioselective arylations of α-amido sulfones with electron-rich arenes through friedel-crafts alkylations catalyzed by ferric chloride hexahydrate: Synthesis of unsymmetrical and bis-symmetrical triarylmethanes
Thirupathi, Ponnaboina,Kim, Sung Soo
experimental part, p. 1798 - 1808 (2010/06/15)
Ferric chloride hexahydrate is a highly efficient catalyst for the regioselective arylation of α-amido sulfones. The products undergo further Friedel-Crafts alkylations with heteroaromatic or electron-rich arenes to afford unsymmetrical or bis-symmetrical
