32891-90-0

Upstream product

• 66-99-9 β-naphthaldehyde 
• 297163-77-0 (4-methoxyphenyl)(ethyl)silanediol 
• 5720-07-0 4-methoxyphenylboronic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-66-3 methoxybenzene 

Downstream Products

• 1582256-37-8 4-chloro-2-((4-methoxyphenyl)(naphthalen-2-yl)methyl)-aniline 
• 1613376-57-0 tert-butyl (naphthalen-2-yl)(phenyl)methyl carbonate 
• 1613376-58-1 C₂₃H₂₄O₃ 
• 1613376-92-3 2-[(4-methoxyphenyl)(naphthalen-2-yl)methyl]-5-phenyloxazole 
• 32891-91-1 2-(4-methoxy-benzyl)-naphthalene 
• 147022-17-1 1-[(4-Methoxy-phenyl)-naphthalen-2-yl-methyl]-1H-imidazole 

Relevant academic research and scientific papers

Visible-Light-Triggered C-C and C-N Bond Formation by C-S Bond Cleavage of Benzylic Thioethers

The cleavage of sulfidic C-S bonds under visible-light irradiation was harnessed to generate carbocations under neutral conditions and synthesize valuable di- and triarylalkanes as well as benzyl amines. To this end, photoredox catalysis and direct photoinduced C-S bond cleavage are used as complementary approaches and participate in the versatility of the general strategy. Extensive mechanistic studies have demonstrated the diversity of the reaction mechanism at work in these different reactions.

The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine

An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.

Synthesis of arylketones by ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids

The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an initial mechanistic investigation.

Palladium-imidazolinium carbene-catalyzed arylation of aldehydes with arylboronic acids in water

The catalytic arylation of aldehydes with arylboronic acids in only water was found to be achieved using the palladium/thioether-imidazolinium chloride system in good to excellent yields. This catalytic process showed high tolerance for a broad range of substrates, giving a variety of carbinol derivatives with 2.0-3.0 mol % of the catalyst.

Addition reaction of arylboronic acids to aldehydes and α,β-unsaturated carbonyl compounds catalyzed by conventional palladium complexes in the presence of chloroform

Arylboronic acids react with aldehydes and α,β-unsaturated carbonyl compounds in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding addition products in good yields, and chiral benzhydrol was obtained with up to 43% e.e. using (S,S)-bppm as a ligand. General palladium complexes have no catalytic activity without chloroform. Because chloroform is essential for this reaction, these reactions would be promoted by dichloromethylpalladium(II) species.

Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether-imidazolinium carbene ligands

(Chemical Equation Presented) Palladium-catalyzed 1,2-addition of potassium aryl- and alkenyltrifluoroborates to aldehydes using thioether- imidazolinium carbene ligands proceeded readily under aqueous conditions. This process tolerated a diverse range of potassium trifluoroborate salts and aldehydes, giving a variety of carbinol derivatives with good to excellent yields.

Palladium-catalyzed addition of arylboronic acids to aldehydes

(Chemical Equation Presented) Arylboronic acids react with aldehydes in the presence of a base and a catalytic amount of a palladium(0) complex with chloroform, affording the corresponding secondary alcohols in good yields. General palladium complexes have no catalytic activity without chloroform. Chloroform is essential for this reaction, and palladium complex that was prepared from Pd(PPh3)4 with CHCl3 showed good catalytic acitivty as well.

Rhodium-catalyzed addition of aryl- and alkenylsilanediols to aldehydes

Arylation and alkenylation of aromatic aldehydes with silanediols is shown to proceed by use of a catalytic amount of rhodium complex. Treatment of ethyl(4-methoxyphenyl)silanediol with benzaldehyde in the presence of 3 mol% of [Rh(OH)(cod)]2 a

Rhodium-catalysed aryl transfer to aldehydes: Counterion effects with nitrogen containing ligands

Cationic rhodium complexes of certain nitrogen-containing ligands exhibit excellent activity in the addition of arylboronic acids to aldehydes. The counterion had a notable effect with the weakly coordinating carborane anion affording a highly active catalyst.