3042-63-5

Basic information

• Product Name: β-(4-methylbenzyl)naphthalene
• Synonyms: β-(4-methylbenzyl)naphthalene
• CAS NO: 3042-63-5
• Molecular Weight: 232.325
• Mol File: 3042-63-5.mol

Chemical Properties

• CAS DataBase Reference: β-(4-methylbenzyl)naphthalene(CAS DataBase Reference)
• NIST Chemistry Reference: β-(4-methylbenzyl)naphthalene(3042-63-5)
• EPA Substance Registry System: β-(4-methylbenzyl)naphthalene(3042-63-5)

Safety Data

• Hazardous Substances Data: 3042-63-5(Hazardous Substances Data)

Upstream product

• 136935-71-2 β-naphthyl-4-methylphenyl-ketone 
• 188404-92-4 (o-methylphenyl)dimethylsilane 
• 624-31-7 4-tolyl iodide 
• 1592-38-7 2-Naphthalenemethanol 
• 21983-00-6 4-methylbenzylboronic acid 
• 17666-88-5 1-(naphthalen-2-yl)butan-1-one 
• 108-88-3 toluene 
• 19350-74-4 2-naphthaldehyde tosylhydrazone 
• 5720-05-8 4-methylphenylboronic acid 
• 66-99-9 β-naphthaldehyde 
• 106-38-7 para-bromotoluene 
• 42101-92-8 2-naphthylmethyl methyl ether 
• 13922-41-3 1-Naphthylboronic acid 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 70557-78-7 2-(4-methylbenzyl)-1,4-naphthoquinone 

Relevant articles and documents

Arylketones as Aryl Donors in Palladium-Catalyzed Suzuki-Miyaura Couplings

Herein, we report the arylation, alkylation, and alkenylation of aryl ketones via a palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. The use of the pyridine-oxazoline ligand is the key to the cleavage of the unstrained C-C bond. The late-stage arylation of aryl ketones derived from drugs and natural products demonstrated the synthetic utility of this protocol.

Selective Conversion of Benzylic Phosphates into Diarylmethanes Through Al(OTf)3-Catalyzed Friedel–Crafts-Type Benzylation

Al(OTf)3 was identified as a high-performance catalyst for Friedel–Crafts-type benzylation using benzylic phosphates as electrophiles. The reaction proceeded even with 0.2 mol-% of the catalyst. A series of diarylmethanes (21 examples) was obtained in moderate to high yield. The catalyst showed unique chemoselectivity, preferentially converting the benzylic phosphate motif, even with a benzylic acetate group existed in the same molecule.

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.

One-pot reductive coupling reactions of acetyl naphthalene derivatives, tosylhydrazide, with arylboronic acids

In this study, a one-pot two-step reductive coupling between acetyl naphthalene derivatives, tosylhydrazide, and arylboronic acids, affording substituted 1(or 2)-(1-phenylethyl)naphthalenes in moderate-to-excellent yields, was reported. Notably, solvent played a crucial role in the coupling of 1-acetyl naphthalene derivatives (toluene) or 2-acetyl naphthalene derivatives (1,4-dioxane) as starting materials. Meanwhile, the scope of this one-pot coupling reaction was extended to 1(or 2)-naphthaldehyde substrates. Particularly, the system was also suitable to synthesize 1(or 2)-(1-phenylethyl)naphthalenes on a multi-gram scale, and was applied in the synthesis of naphthylmethyl substituted carbazolyl compounds.

Practical Cross-Coupling between O-Based Electrophiles and Aryl Bromides via Ni Catalysis

Cross-coupling of various O-based electrophiles with aryl bromides was developed through Ni-catalyzed C-O activation in the presence of magnesium. Beside carboxylates, carbamates, and ethers, phenols exhibited excellent reactivity under modified conditions. This chemistry was featured as a simple and environmentally benign process with low catalyst loading and easy manipulations. The method exhibited broad substrate scopes.

Coupling of arylboronic acids with benzyl halides or mesylates without adding transition metal catalysts

We report herein a transition-metal-free coupling reaction of arylboronic acids with benzyl halides and mesylates for the construction of C(sp2)[sbnd]C(sp3) bonds. A unique feature of this coupling reaction is the formation regioisomers in some cases. Mechanistic studies suggest that this reaction may proceed via an unprecedented Friedel–Crafts-type reaction pathway under base conditions with the assistance of boronic acid moiety.

Nickel/N-Heterocyclic Carbene-Catalyzed Suzuki-Miyaura Type Cross-Coupling of Aryl Carbamates

The utility of N-heterocyclic carbene ligands in nickel-catalyzed Suzuki-Miyaura cross-coupling of aryl esters and carbamates is investigated. Imidazol-2-ylidene bearing 2-adamantyl groups at its nitrogen atoms generates the most active nickel species among the ligands examined, allowing cross-coupling of a range of aryl carbamates and pivalates. Unlike the previously reported system using tricyclohexylphosphine, this protocol is suitable for the cross-coupling using arylboronic esters in addition to arylboronic acids.

Intra- and Intermolecular Nickel-Catalyzed Reductive Cross-Electrophile Coupling Reactions of Benzylic Esters with Aryl Halides

Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions. A range of heterocycles and functional groups are tolerated under the reaction conditions. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described. Crossed off: Nickel-catalyzed cross-electrophile coupling reactions of benzylic esters and aryl halides have been developed. Both inter- and intramolecular variants proceed under mild reaction conditions, and a range of heterocycles and functional groups are tolerated. Additionally, the first example of a stereospecific cross-electrophile coupling of a secondary benzylic ester is described.

Direct cross-coupling of benzyl alcohols to construct diarylmethanes via palladium catalysis

A direct arylation to furnish diarylmethanes from benzyl alcohols was realized through Pd(PPh3)4-catalyzed Suzuki-Miyaura coupling via benzylic C-O activation in the absence of any additives. The arylation is compatible with various functional groups. This development provides an atom- and step-economic way to approach a diarylmethane scaffold under mild and environmentally benign conditions. This journal is

Iridium-catalyzed diborylation of benzylic C-H bonds directed by a hydrosilyl group: Synthesis of 1,1-benzyldiboronate esters

We describe a regioselective diborylation of primary benzylic C-H bonds catalyzed by [Ir(COD)OMe]2 and 4,4′-di-tert-butyl-2,2′- bipyridine (dtbpy). The hydrosilyl group acts as a traceless directing group, providing access to a range of 1,1-benzyldiboronate esters in good yields. Transformations of the 1,1-benzyldiboronate ester products include chemoselective Suzuki-Miyaura cross-couplings and synthesis of tetrasubstituted alkenyl boronate esters.