93327-63-0

Upstream product

• 1062322-50-2 1-(1-naphthyl)-1-(2-hydroxyphenyl)methylenimine 
• 28143-91-1 (1S,2S)-2-amino-1-phenyl-1,3-diol 
• 90-11-9 1-Bromonaphthalene 
• 90-02-8 salicylaldehyde 
• 90-14-2 1-Iodonaphthalene 
• 91-20-3 naphthalene 
• 21615-34-9 2-Methoxybenzoyl chloride 

Relevant academic research and scientific papers

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Asymmetric Transfer Hydrogenation of o-Hydroxyphenyl Ketones: Utilizing Directing Effects That Optimize the Asymmetric Synthesis of Challenging Alcohols

A systematic range of o-hydroxyphenyl ketones were reduced under asymmetric transfer hydrogenation conditions using the C3-tethered catalyst 2. Two directing effects, i.e., an o-hydroxyphenyl coupled to a bulky aromatic on the opposite side of the ketone substrate, combine in a matched manner to deliver reduction products with very high enantiomeric excess.

Ruthenium-Catalyzed Direct Asymmetric Reductive Amination of Diaryl and Sterically Hindered Ketones with Ammonium Salts and H2

A Ru-catalyzed direct asymmetric reductive amination of ortho-OH-substituted diaryl and sterically hindered ketones with ammonium salts is reported. This method represents a straightforward route toward the synthesis of synthetically useful chiral primary diarylmethylamines and sterically hindered benzylamines (up to 97 % yield, 93–>99 % ee). Elaborations of the chiral amine products into bioactive compounds and a chiral ligand were demonstrated through manipulation of the removable and convertible -OH group.

Rhodium-Catalyzed Directing-Group-Assisted Aldehydic C–H Arylations with Aryl Halides

A rhodium-catalyzed general protocol for the directing-group-assisted arylation of aromatic aldehydic C–H bonds was developed. This method involves either hydroxy- or amino-group-directed aldehyde C–H arylation with various aryl halides. A broad synthetic scope for the preparation of 2-hydroxybenzophenones was established with electronically variant salicylaldehydes and aryl halides with chemo- and regioselective possibilities. The developed protocol was also applied in the synthesis of medicinally important 3-salicyloylpyridines in high yields.

PdCl2/DABCO-catalyzed direct arylation of 2-hydroxybenzaldehydes in H2O

In this paper the successful application of DABCO both as base and as ligand for efficient coupling reactions of aryl iodides and bromides with 2-hydroxybenzaldehydes in the presence of catalytic amounts of PdCl2 in water as solvent was introduced.

Palladium-catalyzed direct C-H arylation of 2-hydroxybenzaldehydes with organic halides in neat water

The palladium-catalyzed cross-coupling of 2-hydroxybenzaldehydes with organic halides proceeds in the presence of n-Bu4NBr in H2O producing the corresponding 2-hydroxybenzophenones in high yields.

Water enables transimination between hindered ketimines and β-aminoalcohols and selective protection of a vicinal diamine backbone

Water mediates synthesis of novel hindered Schiff bases via transmination protocol. The feature of the procedure is that it allows both tuning of steric and electronic factors of the substituents and mono-imination of vicinal diamines, which potentially facilitates one-pot approach to unsymmetrical metal ligands. Water mediates access to hindered ketimine ligands incorporating one or two benzylidene moieties and 1,2-diaminocyclohexane.

Palladium-catalyzed coupling reaction of salicylaldehydes with aryl iodides via cleavage of the aldehyde C-H bond

It has been found that the cross-coupling reaction of salicylaldehydes with aryl iodides smoothly proceeds by using a catalyst system of PdCl2/LiCl in the presence of Na2CO3 as base to give the corresponding 2-aroylphenols in good yields, which appears to involve cleavage of the aldehyde C-H bond.