6962-60-3

Usage

InChI:InChI=1/C15H14O2/c1-17-15(16)14-10-6-5-9-13(14)11-12-7-3-2-4-8-12/h2-10H,11H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 612-35-1 2-Benzylbenzoic acid 
• 67-56-1 methanol 
• 606-28-0 methyl o-benzoylbenzoate 
• 100-39-0 benzyl bromide 
• 693232-15-4 2-(methoxycarbonyl)phenylzinc iodide 
• 74-88-4 methyl iodide 
• 51471-72-8 (2-methoxycarbonyl-phenylsulfanyl)-acetic acid 
• 62673-31-8 benzyl(bromo)zinc 
• 85-52-9 2-Benzoylbenzoic acid 
• 1634-04-4 tert-butyl methyl ether 
• 4463-42-7 benzyl boronic acid 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 102876-41-5 Hydroxy-diphenyl-(2-benzyl-phenyl)-methan 
• 1586-00-1 2-(benzyl)benzyl alcohol 
• 60456-75-9 1,1'-diphenyl-1H,1'H-[1,1']biisobenzofuranyl-3,3'-dione 
• 57732-89-5 ortho-benzyl-α,α'-dimethylbenzyl alcohol 
• 123570-21-8 2-Benzyl-<α,α-D2>-benzylalkohol 
• 1586-03-4 2-(2-benzylphenyl)acetonitrile 
• 55276-42-1 2-benzylbenzyl bromide 
• 36374-49-9 2-(2-benzylphenyl)acetic acid 
• 66827-79-0 10,10-Dimethyl-9,10-dihydroanthracene-9-carboxamide 
• 148991-82-6 2-benzyl-N-methoxybenzamide 
• 32832-95-4 2-benzylbenzaldehyde 
• 612-35-1 2-Benzylbenzoic acid 
• 7477-39-6 9,9-diphenyl-9,10-dihydroanthracene 
• 88689-60-5 2,2'-dibenzyl-bibenzyl 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of Benzylic Sulfonium Salts with Aryl Iodides

A nickel-catalyzed cross-electrophile coupling of benzylic sulfonium salts with aryl iodides has been developed, providing direct access to diarylalkanes from readily available and stable coupling partners. Preliminary mechanistic studies suggest that the C-S bond cleavage proceeds through a single-electron transfer process to generate a benzylic radical.

Desulfurative Ni-Catalyzed Reductive Cross-Coupling of Benzyl Mercaptans/Mercaptoacetates with Aryl Halides

The C-S activation and sulfur removal from native thiols is challenging, which limits their application as feedstock materials in organic synthesis despite their natural abundance. Herein, we introduce a per-/polyfluoroaryl moiety, which serves as a redox-active scaffold, into sp3-hybridized thiols to activate the C-S bond. Using a Ni catalyst with MgBr2 as an additive, the S group can be removed to yield an aliphatic radical that can react with an aryl halide in a reductive cross-coupling.

Nickel-Catalyzed Electrochemical C(sp3)?C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**

Reported here is the redox neutral electrochemical C(sp2)?C(sp3) cross-coupling reaction of bench-stable aryl halides or β-bromostyrene (electrophiles) and benzylic trifluoroborates (nucleophiles) using nonprecious, bench-stable NiCl2?glyme/polypyridine catalysts in an undivided cell configuration under ambient conditions. The broad reaction scope and good yields of the Ni-catalyzed electrochemical coupling reactions were confirmed by 50 examples of aryl/β-styrenyl chloride/bromide and benzylic trifluoroborates. Potential applications were demonstrated by electrosynthesis and late-stage functionalization of pharmaceuticals and natural amino acid modification, and three reactions were run on gram-scale in a flow-cell electrolyzer. The electrochemical C?C cross-coupling reactions proceed through an unconventional radical transmetalation mechanism. This method is highly productive and expected to find wide-spread applications in organic synthesis.

Understanding the Chemoselectivity in Palladium-Catalyzed Three-Component Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol

To understand the ligand-controlled palladium-catalyzed coupling of o-bromobenzaldehyde, N-tosylhydrazone, and methanol to give methyl 2-benzylbenzoic ester or methyl ether, we herein investigated the mechanisms which account for how C-C and C-O bonds are

Palladium-Catalyzed Three-Component Coupling Reaction of o-Bromobenzaldehyde, N-Tosylhydrazone, and Methanol

A ligand-controlled palladium-catalyzed three-component reaction of o-bromobenzaldehyde, N-tosylhydrazone, and methanol is described. This reaction uses readily available compounds as starting materials while displaying a broad substrate scope and good functional group compatibility.

Visible-Light-Induced Nickel-Catalyzed Negishi Cross-Couplings by Exogenous-Photosensitizer-Free Photocatalysis

The merging of photoredox and transition-metal catalysis has become one of the most attractive approaches for carbon–carbon bond formation. Such reactions require the use of two organo-transition-metal species, one of which acts as a photosensitizer and t

Iodobenzene-Catalyzed Synthesis of Phenanthridinones via Oxidative C-H Amidation

We report a novel synthesis of phenanthridinones from N-methoxybenzamides using an oxidative C-H amidation reaction at room temperature in open air with modest to excellent yields. This method demonstrated unprecedented substrate scope. In particular, it solved the long-standing challenge in the synthesis of phenanthridinones with sterically demanding substitutions.

One-pot esterification and Ritter reaction: Chemo- and regioselectivity from tert-butyl methyl ether

tert-Butyl methyl ether (TBME) has been effectively used as a reagent for esterification of carboxylic acids. By varying amounts of sulfuric acid, a remarkable regioselectivity in esterification has been demonstrated. Additionally, under the present reaction conditions, one-pot esterification and Ritter reaction are achieved in almost quantitative yield.

Identification of a potent botulinum neurotoxin A protease inhibitor using in situ lead identification chemistry

Botulinum neurotoxins (BoNTs), etiological agents of the deadly food poisoning disease botulism, are the most toxic proteins currently known. By using in situ lead identification chemistry, we have uncovered the first class of inhibitors that displays nanomolar potency. From a 15 μM lead compound, structure-activity relationship studies were performed granting the most potent BoNT/A inhibitor reported to date that displays an inhibition constant of 300 nM.

Tricyclic alkylamides as melatonin receptor ligands with antagonist or inverse agonist activity

This work reports the design and synthesis of novel alkylamides, characterized by a dibenzo[a,d] cycloheptene nucleus, as melatonin (MLT) receptor ligands. The tricyclic scaffold was chosen on the basis of previous quantitative structure-activity studies on MT1 and MT2 antagonists, relating selective MT2 antagonism to the presence of an aromatic substituent out of the plane of the MLT indole ring. Some dibenzo seven-membered structures were thus selected because of the noncoplanar arrangement of their benzene rings, and an alkylamide chain was introduced to fit the requirements for MLT receptor binding, namely, dibenzocycloheptenes with an acylaminoalkyl side chain at position 10 and dibenzoazepines with this side chain originating from the nitrogen atom bridging the two phenyl rings. Binding affinity at human cloned MT1 and MT2 receptors was measured by 2[125I] iodomelatonin displacement assay and intrinsic activity by the GTPγS test. The majority of the compounds were characterized by higher affinity at the MT2 than at the MT 1 receptor and by very low intrinsic activity values, thus confirming the importance of the noncoplanar arrangement of the two aromatic rings for selective MT2 antagonism. Dibenzocycloheptenes generally displayed higher MT1 and MT2 affinity than dibenzoazepines. N-(8-Methoxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-10-ylmethyl)propionamide (4c) and -butyramide (4d) were the most selective MT2 receptor antagonists of the series, with MT2 receptor affinity comparable to that of melatonin and as such among the highest reported in the literature for MLT receptor antagonists. The acetamide derivative 4b produced a noticeable reduction of GTPγS binding at MT2 receptor, thus being among the few inverse agonists described.