86694-47-5Relevant academic research and scientific papers
Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,- c]coumarins and Furo[3,2,- c]pyran-4-ones via Nonsymmetric Triarylmethanes
Girmachew, Selamawit,Kumar, Honnaiah Vijay,Noland, Wayland E.,Sharma, Arjun,Wei, Binyuan
, (2020)
A one-pot synthesis of functionalized 2,3-disubstituted furo[3,2,-c]coumarins and furo[3,2,-c]pyran-4-ones under hydrated ferric sulfate catalysis was performed. It was revealed that the reaction proceeds with intramolecular cyclofunctionalization of nonsymmetric triarylmethanes via ring opening of 2-methylfuran followed by recyclization, resulting in the selective formation of desired products. The versatility of this method was demonstrated via the succinct synthesis of an anticoagulant agent analogue and 2,3-disubstituted benzofurans.
Halogen Bond-Catalyzed Friedel?Crafts Reactions of Furans Using a 2,2’-Bipyridine-Based Catalyst
Zhang, Huimiao,Toy, Patrick H.
supporting information, p. 215 - 221 (2020/12/01)
A halogen bond donor based on a 2,2’-bipyridine framework has been synthesized, and used to catalyze Friedel?Crafts reactions of furans. Electrophiles used successfully in these reactions included various enones, an aldehyde, and a carboxylic acid anhydride. The yields of the reactions were generally good using a moderate catalyst loading (0.025 or 0.1 equiv.) at a relatively low temperature (room temp. or 50 °C) in acetonitrile. The catalyst used was designed with a biaryl scaffold so that if it indeed proved to be an efficient halogen bond donor organocatalyst, an enantioenriched version of it could potentially serve as a stereoselective catalyst. (Figure presented.).
Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C-C Bond-Cleaving Path
Kalita, Gitumoni,Deka, Namrata,Paul, Dipankar,Thapa, Loknath,Dutta, Gitish K.,Chatterjee, Paresh Nath
supporting information, p. 304 - 308 (2020/12/14)
A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO 3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The cata
Anodically Triggered Aldehyde Cation Autocatalysis for Alkylation of Heteroarenes
Liu, Caiyan,Xiao, Zihui,Wu, Shuhua,Shen, Yongli,Yuan, Kedong,Ding, Yi
, p. 1997 - 2001 (2020/02/27)
Alkylation of heteroarenes by using aldehydes is a direct approach to increase molecular complexity, which however often involves the use of stochiometric oxidant, strong acid, and high temperature. This study concerns an energy-efficient electrochemical alkylation of heteroarenes by using aldehydes under mild conditions without mediators. Interestingly, the graphite anode can trigger aldehyde cationic species, which act as the effective autocatalysts to react with a range of heteroarenes to produce the corresponding products with excellent regioselectivity and in high yields. Compared to the traditional electro-synthesis approaches, this electro-triggered reaction provides an electricity-saving and eco-friendly route to high-value chemicals.
A facile iron-catalyzed dual C-C bond cleavage: An approach towards triarylmethanes
Paul, Dipankar,Khatua, Snehadrinarayan,Chatterjee, Paresh Nath
supporting information, p. 10056 - 10065 (2019/07/03)
A facile iron-catalyzed dual C-C bond cleaving reaction involving 1,3-dicarbonyl units along with electron-rich and sterically bulky arenes as efficient carbon-based leaving groups has been developed. The scope of the dual C-C bond breaking reaction was s
Synthesis method of triarylmethane and derivative thereof under solvent-free condition
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Paragraph 0016; 0017, (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.
Radical Relatives: Facile Oxidation of Hetero-Diarylmethene Anions to Neutral Radicals
Curcio, Massimiliano,Henschel, Daniel,Hüttenschmidt, Mareike,Sproules, Stephen,Love, Jason B.
, p. 9592 - 9600 (2018/08/28)
Furan and thiophene diarylmethenes are potential redox-active ligands for metal centers that could be exploited in the development of nontraditional, stoichiometric, and catalytic redox reactions. As such, we describe here the selective meso-deprotonations of dithiophene, difuran, and diimine-difuran diarylmethanes to form the ?-conjugated anions, for which only the diimino-difuryl anion is truly isolable and studied by X-ray crystallography. In all cases, facile one-electron oxidation of these anions occurs, which allows the isolation of the neutral dithienyl and diimino-difuryl radicals. UV-Visible and time-dependent density functional theory studies reveal that the oxidation of the dithienyl anion to its radical is associated with an increase in the highest (singly) occupied molecular orbital-lowest unoccupied molecular orbital gap, evident through a hypsochromic shift of the main absorption band in the electronic spectrum, whereas oxidation of the diimino-difuryl anion causes only minor spectroscopic changes. Electrochemical studies support the stability of the radicals with respect to the anion, showing strongly negative oxidation potentials. The control of the redox activity of these diarylmethene carbanions through variation of the nature of the substituents, donor-atom, and the conjugated ?-system and their potential as ligands for redox-inert metal centers makes them intriguing candidates as noninnocent partners for redox reactions.
Lewis acid-mediated mono- and bis-addition of C-nucleophiles to 1,3-dioxolan-4-ones
Shcherbinin, Vitaly A.,Konshin, Valery V.
, p. 3005 - 3009 (2018/07/06)
The reactions of 1,3-dioxolan-4-ones, readily available from α-hydroxy acids and aldehydes, with C-nucleophiles are described. Two possible reaction pathways resulting in O-substituted acids and tri-(hetero)arylmethanes are shown.
CuBr2-catalyzed alkylation of furans with benzyl alcohols and benzaldehydes. Domino reactions including this alkylation as a key step
Makarov, Anton S.,Kekhvaeva, Anna E.,Hall, Christopher J.J.,Price, Daniel R.,Trushkov, Igor V.,Uchuskin, Maxim G.
, p. 7042 - 7053 (2017/11/13)
A CuBr2-catalyzed alkylation of furans with a broad scope of benzyl alcohols and benzaldehydes is reported. Reaction proceeds efficiently under mild reaction conditions requiring no inert atmosphere or other precautions. Moreover, it is shown that CuBr2 catalyzes domino reactions of furans with benzyl alcohols or benzaldehydes bearing a nucleophilic moiety in the ortho-position. These protocols offer a practical approach to densely substituted heterocyclic motifs from easily available furans.
Facile synthesis of nonsymmetrical heteroaryl-substituted triarylmethanes: Via the FeCl3·6H2O-catalyzed two-step Friedel-Crafts-type reaction
Ruengsangtongkul,Taprasert,Sirion,Jaratjaroonphong
, p. 8493 - 8502 (2016/09/28)
The FeCl3·6H2O-catalyzed three-component aza-Friedel-Crafts reaction of aromatic/heteroaromatic compounds, aromatic aldehydes and tert-butyl carbamate was reported. The subsequent Friedel-Crafts-type alkylation of the resulting tert-
