796874-06-1

Upstream product

• 108-95-2 phenol 
• 796874-03-8 (4-methoxyphenyl)(phenanthren-9-yl)methanol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 1609277-63-5 (4-benzyloxyphenyl)(4-methoxyphenyl)methyl phenyl sulfone 
• 1609277-78-2 (4-benzyloxyphenyl)(4-methoxyphenyl)(9-phenanthryl)methane 
• 1609277-60-2 4-benzyloxyphenylmethyl phenyl sulfone 
• 6793-92-6 p-benzyloxyphenylbromide 
• 4707-71-5 Phenanthrene-9-carboxaldehyde 
• 74-88-4 methyl iodide 
• 796874-25-4 4-[(4-hydroxyphenyl)phenanthren-9-ylmethyl]phenol 
• 128-39-2 2,6-di-tert-butylphenol 
• 100-66-3 methoxybenzene 
• 14202-31-4 4-methoxybenzaldehyde-1,1-diacetate 
• 71112-64-6 9-phenanthrylmagnesium bromide 

Downstream Products

• 870719-91-8 2-{4-[(4-methoxy-phenyl)-phenanthren-9-yl-methyl]-phenoxymethyl}-oxirane 

Relevant academic research and scientific papers

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.

Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents

A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.

Sequential Selective C?H and C(sp3)?+P Bond Functionalizations: An Entry to Bioactive Arylated Scaffolds

Organophosphonium salts containing C(sp3)?+P bonds are among the most utilized reagents in organic synthesis for constructing C?C double bonds. However, their use as C-selective electrophilic groups is rare. Here, we explore an efficient and general transition-metal-free method for sequential chemo- and regioselective C?H and C(sp3)?+P bond functionalizations. In the present study, C?H alkylation resulting in the synthesis of benzhydryl triarylphosphonium salts was achieved by one-pot, four-component cross-coupling reactions of simple and commercially available starting materials. The utility of the resulting phosphonium salt building blocks was demonstrated by the chemoselective post-functionalization of benzylic C(sp3)?+PPh3 groups to achieve aminations, thiolations, and arylations. In this way, benzhydrylamines, benzhydrylthioethers, and triarylmethanes, structural motifs that are present in many pharmaceuticals and agrochemicals, are readily accessed. These include the synthesis of two anticancer agents from simple materials in only two to three steps. Additionally, a protocol for late-stage functionalization of bioactive drugs has been developed using benzhydrylphosphonium salts. This new approach should provide novel transformations for application in both academic and pharmaceutical research.

Transition-Metal-Free Arylation and Alkylation of Diarylmethyl p-Tolyl Sulfones with Zinc Reagents

The transition-metal-free synthesis of unsymmetrical and highly functionalized triarylmethanes through arylation of the situ generated o-QMs from diarylmethyl p-tolyl sulfones with aryl zinc reagents is described. Alkyl zinc reagents are also well tolerated in this reaction. Additionally, the straightforward synthesis of the analogue of the antituberculosis agent A and the key precursor of the anti-breast-cancer agent B are achieved by this strategy.

Copper-mediated arylation with arylboronic acids: Facile and modular synthesis of triarylmethanes

A facile and modular synthesis of triarylmethanes was achieved in good yield via a two-step sequence in which the final step is the copper(II)-catalyzed arylation of diarylmethanols with arylboronic acids. By using this protocol a variety of symmetrical and unsymmetrical triarylmethanes were synthesized. As an application of the newly developed methodology, we demonstrate a highyielding synthesis of the triarylmethane intermediate towards an anti-breast-cancer drug candidate.

Modular synthesis of triarylmethanes through palladium-catalyzed sequential arylation of methyl phenyl sulfone

Triarylmethanes, which are valuable structures in materials, sensing and pharmaceuticals, have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. This method provides a new synthetic approach to multisubstituted triarylmethanes using readily available haloarenes and aryl boronic acids, and is also valuable for the preparation of unexplored triarylmethane-based materials and pharmaceuticals. Unsymmetric triarylmethanes have been synthesized starting from methyl phenyl sulfone as an inexpensive and readily available template. The three aryl groups were installed through two sequential palladium-catalyzed C-H arylation reactions, followed by an arylative desulfonation. Copyright

Effect of substituents on diarylmethanes for antitubercular activity

Aminoalkyl derivatives of diarylmethanes were prepared using Grignard, Friedel-Crafts arylation and aminohydrochloride chain formation reactions. These series of compounds were evaluated against Mycobacterium tuberculosis H37Rv and s

Diaryloxy methano phenanthrenes: A new class of antituberculosis agents

A new series of diaryloxy methano phenanthrenes were prepared through tertiary-aminoalkylations of [(methoxy-phenyl)-phenanthren-9-yl-methyl]-phenols obtained from Friedel-Crafts alkylations on (methoxy-phenyl)-phenanthren-9-yl- methanols. These series of