6336-03-4

Upstream product

• 104-57-4 benzyl formate 
• 72594-62-8 naphthalen-1-yl-carbamic acid tert-butyl ester 
• 134-32-7 1-amino-naphthalene 
• 501-53-1 benzyl chloroformate 

Downstream Products

• 134-32-7 1-amino-naphthalene 
• 2216-68-4 N-methylnaphthalen-1-amine 
• 1292296-59-3 methylnaphthalen-1-ylthiocarbamic acid (S)-1-phenylethyl ester 
• 1292296-81-1 (S)-1-naphthalen-1-yl-1-phenylethanethiol 
• 1292296-71-9 methylthiocarbamic acid (S)-1-naphthalen-1-yl-1-phenylethyl ester 
• 352208-32-3 4-[3-(3-tert-butyl-5-methoxy-2-methoxymethoxy-phenyl)-1-naphthalen-1-yl-ureido]-butyric acid ethyl ester 

Relevant academic research and scientific papers

Catalytic Reductions Without External Hydrogen Gas: Broad Scope Hydrogenations with Tetrahydroxydiboron and a Tertiary Amine

Facile reduction of aryl halides with a combination of 5% Pd/C, B2(OH)4, and 4-methylmorpholine is reported. Aryl bromides, iodides, and chlorides were efficiently reduced. Aryl dihalides containing two different halogen atoms underwent selective reduction: I over Br and Cl, and Br over Cl. Beyond these, aryl triflates were efficiently reduced. This combination was broadly general, effectuating reductions of benzylic halides and ethers, alkenes, alkynes, aldehydes, and azides, as well as for N-Cbz deprotection. A cyano group was unaffected, but a nitro group and a ketone underwent reduction to a low extent. When B2(OD)4 was used for aryl halide reduction, a significant amount of deuteriation occurred. However, H atom incorporation competed and increased in slower reactions. 4-Methylmorpholine was identified as a possible source of H atoms in this, but a combination of only 4-methylmorpholine and Pd/C did not result in reduction. Hydrogen gas has been observed to form with this reagent combination. Experiments aimed at understanding the chemistry led to the proposal of a plausible mechanism and to the identification of N,N-bis(methyl-d3)pyridin-4-amine (DMAP-d6) and B2(OD)4 as an effective combination for full aromatic deuteriation. (Figure presented.).

One stone two birds: Cobalt-catalyzed in situ generation of isocyanates and benzyl alcohols for the synthesis of N-aryl carbamates

An efficient method for the synthesis of N-aryl carbamates from N-Boc-protected amines has been developed. The cobalt-catalyzed in situ generation of isocyanates from N-Boc-protected amines and benzyl alcohols from benzyl formates has been achieved for the first time, which in turn furnished the corresponding benzyl carbamates in moderate to high yields. The reaction was catalyzed by CoI2 with tris-(4-dimethylaminophenyl)-phosphine as the ligand and zinc powder as the reductant. The developed reaction conditions were found to be compatible for aromatic amines with both electron-donating and -withdrawing substituents.

Silver-Catalyzed para -Selective C-H Amination of 1-Naphthylamides with Azodicarboxylates at Room Temperature

A simple and efficient protocol for para -selective C-H amination of 1-naphthylamide derivatives under silver catalysis is described. This reaction system could proceed without the help of directing group and a broad range of substrates were proved to be well tolerated. In addition, control experiments suggested that this reaction might not proceed via a single-electron-transfer process.

Enantioselective synthesis of tertiary thiols by intramolecular arylation of lithiated thiocarbamates

Lithiation of N-aryl S-α-alkylbenzyl thiocarbamates leads to rearrangement with migration of the N-aryl ring to the anionic centre α to S, a process which generally proceeds with ca. 98% retention of stereochemistry and returns chiral benzylic tertiary thiols in high enantiomeric ratios.

Microwave-assisted carbamoylation of amines

The influence of microwave irradiation on the reaction of various amines with benzyl chloroformate and di-tert-butyl dicarbonate was investigated. Microwave irradiation was successfully applied to the carbamoylation of several nonfunctionalized and functionalized amines, including amino acids and nucleobases, leading to satisfactory to high product conversion within very short reaction times. Copyright Taylor & Francis Group, LLC.