2116-36-1

Usage

Synthesis Reference(s)

Synthesis, p. 770, 1986 DOI: 10.1055/s-1986-31773

Upstream product

• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 71-43-2 benzene 
• 108-86-1 bromobenzene 
• 100-52-7 benzaldehyde 
• 10034-85-2 hydrogen iodide 
• 146285-52-1 (4-bromobenzyl)-2,2,2-trichloroacetimidate 
• 882980-43-0 2-benzyloxy-1-methylpyridinium triflate 
• 65-85-0 benzoic acid 
• 1122-91-4 4-bromo-benzaldehyde 
• 100-58-3 phenylmagnesium bromide 
• 603-33-8 triphenylbismuthane 
• 57477-93-7 hydrazone of p-bromobenzaldehyde 
• 98-80-6 phenylboronic acid 

Downstream Products

• 572910-05-5 4,4'-dibenzyldiphenyl 
• 100975-75-5 2-(4-benzylphenyl)ethan-1-ol 
• 2116-37-2 4-(Fluorenyl-⁽⁹⁾)-diphenylmethan 
• 56311-14-9 2-(4-benzyl-phenyl)-[1,3,6,2]dioxazaborocane 
• 65189-90-4 4-(1-hydroxyethyl)benzophenone 
• 96968-51-3 1,1-Bis--2,2,2-trichlor-ethan 
• 96264-88-9 1-(p-Bromphenyl)-1-<(p-(4-brombenzyl)phenyl)-2,2,2-trichloraethan 
• 96709-62-5 1.4-Di-<(p-brombenzyl)-benzoyl>-benzol 
• 97923-17-6 α,α'-Di-(4-(p-brombenzyl)-phenyl)-p-xylol 
• 101-81-5 Diphenylmethane 
• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 121805-26-3 4-benzyl-phenethyl bromide 
• 108714-30-3 4-benzyl-phenethylamine 
• 101286-46-8 (4-benzyl-phenethyl)-methyl-amine 

Relevant academic research and scientific papers

Borane-catalyzed C(sp3)-F bond arylation and esterification enabled by transborylation

The activation and functionalization of carbon- fluorine bonds represent a significant synthetic challenge, given the high thermodynamic barrier to C-F bond cleavage. Stoichiometric hydridoborane-mediated C-F functionalization has recently emerged, but is yet to be rendered catalytic. Herein, the borane-catalyzed coupling of alkyl fluorides with arenes (carbon-carbon bond formation) and carboxylic acids (carbon-oxygen bond formation) has been developed using transborylation reactions to achieve catalytic turnover. Successful C-C and C-O coupling across a variety of structurally and electronically differentiated arenes and carboxylic acids was achieved using 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) as the catalyst and pinacolborane (HBpin), with broad functional group tolerance. Experimental and computational studies suggest a mechanistic dichotomy for the carbon-carbon and carbon-oxygen coupling reactions. B-F transborylation (B-F/B-H metathesis) between F-B-9-BBN and HBpin enabled catalytic turnover for carbon-carbon bond formation, whereas direct exchange between the alkyl fluoride and acyloxyboronic ester (C-F/B-O metathesis) was proposed for carbon-oxygen coupling, where H-B-9-BBN catalyzed the dehydrocoupling of the carboxylic acid with HBpin.

Nitrenium Salts in Lewis Acid Catalysis

Molecular compounds featuring nitrogen atoms are typically regarded as Lewis bases and are extensively employed as donor ligands in coordination chemistry or as nucleophiles in organic chemistry. By contrast, electrophilic nitrogen-containing compounds are much rarer. Nitrenium cations are a new family of nitrogen-based Lewis acids, the reactivity of which remains largely unexplored. In this work, nitrenium ions are explored as catalysts in five organic transformations. These reactions are the first examples of Lewis acid catalysis employing nitrogen as the site of substrate activation. Moreover, these compounds are readily accessed from commercially available reagents and exhibit remarkable stability toward moisture, allowing for benchtop transformations without the need to pretreat solvents.

Phosphonic acid mediated practical dehalogenation and benzylation with benzyl halides

For the first time, by using H3PO3/I2 system, various benzyl chlorides, bromides and iodides were dehalogenated successfully. In the presence of H3PO3, benzyl halides underwent electrophilic substitution reactions with electron-rich arenes, leading to a broad range of diarylmethanes in good yields. These transformations feature green, cheap reducing reagents and metal-free conditions. A possible mechanism was proposed.

Carbonyl and olefin hydrosilylation mediated by an air-stable phosphorus(iii) dication under mild conditions

The readily-accessible, air-stable Lewis acid [(terpy)PPh][B(C6F5)4]21 is shown to mediate the hydrosilylation of aldehydes, ketones, and olefins. The utility and mechanism of these hydrosilylations are considered.

Super electron donor-mediated reductive desulfurization reactions

The desulfurization of thioacetals and thioethers by a pyridine-derived electron donor is described. This methodology provides efficient access to the reduced products in high yields and does not require the use of transition-metals, elemental alkali-metals, or hydrogen atom donors.

An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols

This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).

Chlorotrimethylsilane and Sodium Iodide: A Remarkable Metal-Free Association for the Desulfurization of Benzylic Dithioketals under Mild Conditions

A novel metal-free process allowing the reductive desulfurization of various benzylic dithioketals to afford diarylmethane and benzylester derivatives with good to excellent yields is reported. At room temperature, this mild reduction process requires only the use of TMSCl and NaI in CH2Cl2 and tolerates a large variety of functional groups. (Figure presented.).

A Zinc Catalyzed C(sp3)?C(sp2) Suzuki–Miyaura Cross-Coupling Reaction Mediated by Aryl-Zincates

The Suzuki–Miyaura (SM) reaction is one of the most important methods for C?C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross-coupling of benzyl bromides with aryl borates is catalyzed by ZnBr2, in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross-coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.

Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes

A Cu-catalyzed method has been identified for selective oxidative arylation of benzylic C-H bonds with arylboronic esters. The resulting 1,1-diarylalkanes are accessed directly from inexpensive alkylarenes containing primary and secondary benzylic C-H bonds, such as toluene or ethylbenzene. All catalyst components are commercially available at low cost, and the arylboronic esters are either commercially available or easily accessible from the commercially available boronic acids. The potential utility of these methods in medicinal chemistry applications is highlighted.

Synthetic method of diarylmethanes

The invention discloses a synthetic method of diarylmethanes. The method is characterized in that benzyl pseudohalide and aromatic boric acid are reacted in an organic solvent under alkaline condition. The method employs easily available raw materials, conversion is realized under effect of no transition metal catalysis, water-free and oxygen-free are not required, Lewis acid catalysis is not required, the method has wide substrate universality, and various substituted diarylmethanes can be synthesized by the method.