54921-79-8

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 670249-10-2 (2,4,6-trimethoxyphenyl)phenylmethanol 
• 100-52-7 benzaldehyde 
• 64-17-5 ethanol 
• 876498-18-9 Hydroxy-phenyl-bis-(2,4,6-trimethoxy-phenyl)-methan 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 51608-60-7 phenyl N-tosyl imine 

Downstream Products

• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 876498-18-9 Hydroxy-phenyl-bis-(2,4,6-trimethoxy-phenyl)-methan 

Relevant academic research and scientific papers

A recyclable Amberlyst-15-catalyzed three-component reaction in water to synthesize diarylmethyl sulfones

A recyclable Amberlyst-15-catalyzed three-component reaction in water was developed to synthesize asymmetric diarylmethyl sulfones in good to excellent yields with a wide substrate scope. Asymmetric diarylmethyl sulfones were prepared via C-C and C-S bond

Development of Transition-Metal-Free Lewis Acid-Initiated Double Arylation of Aldehyde: A Facile Approach Towards the Total Synthesis of Anti-Breast-Cancer Agent

This work describes a mild and robust double hydroarylation strategy for the synthesis of symmetrical /unsymmetrical diaryl- and triarylmethanes in excellent yields using Lambert salt (0.2–1.0 mol%). Despite the anticipated challenges associated with controlling selective product formation, unsymmetrical diaryl- and triarylmethanes products are obtained unprecedentedly. A highly efficient gram scale reaction has also been reported (TON for symmetrical product=475 and for unsymmetrical product=390). The synthetic utility of the methodology is demonstrated by the preparation of several unexplored diaryl- and triarylmethane-based biologically relevant molecules, such as arundine, vibrindole A, turbomycin B, and certain anti-inflammatory agents. A total synthesis of an anti-breast-cancer agent is also demonstrated. Control experiments, Hammett analysis, HRMS and GC-MS studies reveal the reaction intermediates and reaction mechanism.

Chemoselective Nucleophilic Functionalizations of Aromatic Aldehydes and Acetals via Pyridinium Salt Intermediates

The development of a novel chemoselective functionalization can diversify the strategy for synthesizing the target molecules. The perfect chemoselectivity between aromatic and aliphatic aldehydes is difficult to achieve by the previous methods. The aromatic aldehyde-selective nucleophilic addition in the presence of aliphatic aldehydes was newly accomplished. Namely, the aromatic aldehyde-selective nucleophilic addition using arenes and allyl silanes proceeded in the presence of trialkylsilyl triflate and 2,2′-bipyridyl, while the aliphatic aldehydes completely remained unchanged. The reactive pyridinium-type salt intermediate derived from an aromatic aldehyde chemoselectively underwent the nucleophilic substitution. Moreover, the aromatic acetals as the protected aldehydes could be directly transformed into similar pyridinium salt intermediates, which reacted with various nucleophiles coexisting with the aliphatic aldehydes.

Lewis acid-mediated mono- and bis-addition of C-nucleophiles to 1,3-dioxolan-4-ones

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.

Green synthesis and antiviral activity of novel triarylmethane derivatives via Friedel-Crafts alkylation by polyethylene glycol (PEG-400)

A series of novel triarylmethane derivatives (3a-j) were synthesized by a one-pot, two-component method via Friedel-Crafts alkylation of various electron-rich arenes (1a-j) with a wide variety of aldehydes (2a-j) in presence of the polyethylene glycol (PEG-400) as a green solvent at 50-60 °C in good to excellent yields (76-96 %). Their structures were confirmed by FT-IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. All the triarylmethanes were tested and evaluated for their antiviral and antifungal activities. Compounds 3b, 3f, 3g and 3i exhibited highest antiviral activities against tobacco mosaic virus (TMV).

A rapid, highly efficient, and general protocol for the synthesis of functionalized triarylmethanes: A straightforward access for the synthesis of (-)-tatarinoid C

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.

SnCl2 insertion into Ir-Cl and Rh-Cl bonds: Synthesis, characterization and catalytic activity of three-legged piano-stool trichlorostannyl iridium and rhodium complexes

Facile insertion reaction of SnCl2 across pentamethylcyclopentadienyl complexes of Ir(III) and Rh(III) resulted in the formation of Ir-SnCl3 and Rh-SnCl3 heterobimetallic complexes. Treatment of SnCl2 with [Cp*IrCl2] 2 and [Cp*Ir(NH2tBu)Cl2] afforded [Cp*Ir(SnCl3)2{SnCl2(H 2O)2}] (1) and [Cp*Ir(SnCl3) 3][NH3tBu] (3), respectively. Similarities in NMR data for complexes 1 and 3 suggested that complex 1 converts to anionic [Cp*Ir(SnCl3)3] species in solution via rapid chloride exchange. Similarly, insertion reaction of SnCl2 with [Cp*Ir(PPh3)Cl2] and [Cp*Rh(PPh 3)Cl2] afforded single insertion complex [Cp*Ir(PPh3)(SnCl3)Cl] (2) and double insertion complex [Cp*Rh(PPh3)(SnCl3)2] (4), respectively. All these new complexes were characterized by multinuclear NMR spectroscopy, while complexes 1, 3 and 4 were structurally characterized by single crystal X-ray diffraction technique. Complexes 1-4 were also tested as catalyst for bisarylation of aldehyde with arene and it was observed that only complexes 1 and 3 were active. Scope of this organic reaction was examined for different arenes and heteroarenes and in all the cases very good yields of triarylmethane derivatives were achieved.

Heterobimetallic Ir-Sn catalysis: Aza-Friedel-Crafts reaction of N-sulfonyl aldimines

The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)] 2 catalyzes the aza-Friedel-Crafts reaction of 1,3,5- trimethoxybenzene, as well as substituted indoles with N-sulfonyl aldimines leading to the formation of diarylamines and triarylmethanes in good yields. The symmetrical triarylmethanes were also obtained from diarylamines and suitable nucleophiles via simultaneous cleavage of sp3 C-N bond and elimination of 1,3,5-trimethoxybenzene.

Room-temperature bismuth-catalyzed bis-arylation of carbonyl compounds with aryl ethers and phenols

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

Iodine-catalyzed, one-pot, three-component aza-Friedel-Crafts reaction of electron-rich arenes with aldehyde/carbamate combinations

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'