102459-18-7

Upstream product

• 932-87-6 1-Bromo-2-phenylacetylene 
• 103-49-1 dibenzylamine 
• 201230-82-2 carbon monoxide 
• 959571-89-2 N-isopropyl-N-(4-methylbenzyl)propan-2-amine 
• 620-40-6 tribenzylamine 
• 103-82-2 phenylacetic acid 
• 67-56-1 methanol 
• 58288-30-5 N,N,N′,N′-tetrabenzylmethanediamine 
• 60-12-8 2-phenylethanol 
• 61821-54-3 N,N-dibenzyl-2-phenylethanethioamide 
• 108-88-3 toluene 
• 536-74-3 phenylacetylene 
• 103-80-0 phenylacetyl chloride 
• 24648-07-5 2-Phenyl-1,3,3-trichlorocyclopropene 

Downstream Products

• 6109-33-7 4-phenyl-1,4-dihydroisoquinolin-3(2H)-one 
• 1598387-18-8 N,N-dibenzyl-3,3-difluoro-2-phenyl-3-(trimethylsilyl)propanamide 
• 1262617-51-5 N,N-dibenzyl-N-(1-benzylcyclopropyl)amine 

Relevant academic research and scientific papers

Visible-light-mediated eosin y catalyzed aerobic desulfurization of thioamides into amides

A novel method for the metal-free efficient synthesis of amides from thioamides using visible light and in an air atmosphere in the presence of eosin Y as an organophotoredox catalyst is reported. The protocol involves aerobic desulfurization-oxygenation of thioamides into amides in good to excellent yields at r.t. in a one-pot operation under mild conditions with the formation of nontoxic elemental sulfur as the only by-product. On the basis of several relevant experiments performed, it has been shown that the present photooxidation does not involve a singlet oxygen and accordingly a plausible organocatalytic photoredox mechanism is proposed.

Ammonia-borane as a Catalyst for the Direct Amidation of Carboxylic Acids

Ammonia-borane serves as an efficient substoichiometric (10%) precatalyst for the direct amidation of both aromatic and aliphatic carboxylic acids. In situ generation of amine-boranes precedes the amidation and, unlike the amidation with stoichiometric amine-boranes, this process is facile with 1 equiv of the acid. This methodology has high functional group tolerance and chromatography-free purification but is not amenable for esterification. The latter feature has been exploited to prepare hydroxyl- and thiol-containing amides.

Efficient and accessible silane-mediated direct amide coupling of carboxylic acids and amines

A straightforward method for the direct synthesis of amides from amines and carboxylic acids without exclusion of air or moisture using diphenylsilane with N-methylpyrrolidine has been developed. Various amides are made efficiently, and broad functional group compatibility is shown through a Glorius robustness study. A gram-scale synthesis demonstrates the scalability of this method. This journal is

Enantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Br?nsted Acid Catalysis

The synthesis of α-aryl-β2-amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Br?nsted acid catalysis is demonstrated. The scope and limitatio

Amide bond synthesis via silver(I) N-heterocyclic carbene-catalyzed and tert-butyl hydroperoxide-mediated oxidative coupling of alcohols with amines under base free conditions

We present a base free method for amide bond construction via oxidative coupling of alcohols with amines catalyzed by Silver(I) N-heterocyclic carbenes (Ag(I)-NHCs) and mediated by tert-butyl hydroperoxide (TBHP) in ethanol. The results of controlled experiments suggest that the oxidative coupling proceeds through the formation of aldehyde, then subsequent attack by amine to give hemiaminal, which can then be oxidized to amide.

Flexible and Chemoselective Oxidation of Amides to α-Keto Amides and α-Hydroxy Amides

A suite of flexible and chemoselective methods for the transition-metal-free oxidation of amides to α-keto amides and α-hydroxy amides is presented. These highly valuable motifs are accessed in good to excellent yields and stereoselectivities with high functional group tolerance. The utility of the method is showcased by the formal synthesis of a potent histone deacetylase inhibitor.

An Efficient One–pot Procedure for the Direct Preparation of 4,5-Dihydroisoxazoles from Amides

A Mo(CO)6 (molybdenumhexacarbonyl) catalyzed reductive functionalization of amides to afford 5-amino substituted 4,5-dihydroisoxazoles is presented. The reduction of amides generates reactive enamines, which upon the addition of hydroximinoyl chlorides and base undergoes a 1,3-dipolar cycloaddition reaction that gives access to the desired heterocyclic compounds. The transformation of amides is highly chemoselective and tolerates functional groups such as nitro, nitriles, esters, and ketones. Furthermore, a versatile scope of 4,5-dihydroisoxazoles derived from a variety of hydroximinoyl chlorides and amides is demonstrated. (Figure presented.).

Phototriggered Dehydration Condensation Using an Aminocyclopropenone

A phototriggered dehydration condensation using an aminocyclopropenone has been developed. The UV irradiation of an aminocyclopropenone generated a highly reactive ynamine in situ and the dehydration condensation of a carboxylic acid and an amine coexisting in the reaction solution smoothly proceeded to afford an amide. This reaction is completely controllable by the ON/OFF states of a UV lamp.

Charge-Transfer Complex Promoted C-N Bond Activation for Ni-Catalyzed Carbonylation

A new strategy was developed for activation of C-N bond via formation of an amine-I2 charge-transfer complex, which facilitates the inert C-N bond activation via oxidative addition with Ni(0). This strategy has been successfully applied in the Ni-catalyzed carbonylation of benzylamines via direct insertion of CO into the C-N bond, which provided a straightforward and rapid approach to arylacetamides in the presence of catalytic amounts of I2 and Ni catalyst. Mechanistic studies suggested that a benzyl radical generated via the oxidative addition was involved in the present reaction.

Metal-Free Formal Oxidative C?C Coupling by In Situ Generation of an Enolonium Species

Much contemporary organic synthesis relies on transformations that are driven by the intrinsic, so-called “natural”, polarity of chemical bonds and reactive centers. The design of unconventionally polarized synthons is a highly desirable strategy, as it generally enables unprecedented retrosynthetic disconnections for the synthesis of complex substances. Whereas the umpolung of carbonyl centers is a well-known strategy, polarity reversal at the α-position of a carbonyl group is much rarer. Herein, we report the design of a novel electrophilic enolonium species and its application in efficient and chemoselective, metal-free oxidative C?C coupling.