38491-27-9

Upstream product

• 99-76-3 methyl 4-hydroxylbenzoate 
• 79-44-7 N,N-Dimethylcarbamoyl chloride 
• 68-12-2 N,N-dimethyl-formamide 
• 74721-70-3 dimethyl 4,4′-(carbonylbis(oxy))dibenzoate 
• 124-40-3 dimethyl amine 

Downstream Products

• 60034-85-7 N,N,2,5-tetramethylbenzamide 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 1631050-55-9 methyl 4-((dimethylcarbamoyl)oxy)-3-hydroxybenzoate 
• 1534364-30-1 methyl 3-chloro-4-((dimethylcarbamoyl)oxy)benzoate 
• 1380586-40-2 methyl 3-bromo-4-(dimethylcarbamoyloxy)benzoate 
• 905966-40-7 methyl 4-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzoate 
• 720-75-2 methyl 4-phenylbenzoate 

Relevant academic research and scientific papers

Copper porphyrin-catalyzed C(sp2)—O bond construction via coupling phenols with formamides

Copper porphyrin-catalyzed construction of C(sp2)—O bond via coupling formamides with phenols was achieved firstly. A broad range of substrates afforded various carbamates in moderate to good yields with good functional group tolerance at low catalyst loading. Intermolecular competing kinetic isotope effect experiment indicated that the generation of formamide radical is the rate-determining step of current cross-dehydrogenative coupling (CDC) reaction. The research extends the application of metalloporphyrin in CDC reaction.

The construction of C(sp3)–O bond via copper porphyrin catalyzed cross-dehydrogenative coupling reaction: Substituent and electronic effect of the catalysts

The push-pull electronic and steric effect of copper porphyrin catalysts on the cross-dehydrogenative coupling (CDC) reaction between the hydroxyl group of phenol substrates and C(sp3)-H bond have been investigated. Results showed that copper porphyrin bearing electron-withdrawing, bulky steric hindrance or heteroatom of pyridyl groups could increase the catalytic activity in the reaction. 5,10,15,20-(tetrakis(4-pyridyl)porphyrin)copper (CuTPyP) was found the best among all tested catalysts. Phenol substrates bearing various functional groups afforded moderate to excellent yields (99%). Significantly, as compared to other tested copper porphyrins, CuTPyP not only exhibited remarkable higher activity but also could shorten the reaction time from 12 to 6 h.

Construction of C–O bond via cross-dehydrogenative coupling of sp [ 3] C–H bond with phenols catalyzed by copper porphyrin

Copper porphyrin-catalyzed construction of ether bond by cross-dehydrogenative coupling of sp [3] C–H bond with phenols bearing electron-withdrawing groups (EWG) was described for the first time. A broad range of substrates afforded different acetals in m

Tandem buildup of complexity of aromatic molecules through multiple successive electrophile generation in one pot, controlled by varying the reaction temperature

While some sequential electrophilic aromatic substitution reactions, known as tandem/domino/cascade reactions, have been reported for the construction of aromatic single skeletons, one of the most interesting and challenging possibilities remains the one-pot build-up of a complex aromatic molecule from multiple starting components, i.e., ultimately multi-component electrophilic aromatic substitution reactions. In this work, we show how tuning of the leaving group ability of phenolate derivatives from carbamates and esters provides a way to successively generate multiple unmasked electrophiles in a controlled manner in one pot, simply by varying the temperature. Here, we demonstrate the autonomous formation of up to three bonds in one pot and formation of two bonds arising from a three-component electrophilic aromatic substitution reaction. This result provides a proof-of-concept of our strategy applicable for the self-directed construction of complex aromatic structures from multiple simple molecules, which can be a potential avenue to realize multi-component electrophilic aromatic substitution reactions.

A general approach towards catechol and pyrogallol through ruthenium- and palladium-catalyzed C-H hydroxylation by weak coordination

An efficient ruthenium(II)- and palladium(II)-catalyzed C-H hydroxylation of aryl carbamates has been developed for the facile synthesis of catechols and pyrogallols. The reaction demonstrates excellent reactivity, regio- and chemoselectivity, good functional group compatibility and high yields. The practicality of this method has been proved by a gram-scale synthesis.

Palladium catalyzed C-H functionalization of O-arylcarbamates: Selective ortho -bromination using NBS

A series of cyclometalated palladium complexes derived from O-phenylcarbamates has been synthesized by the reaction of the respective carbamates with Pd(OAc)2 in the presence of acids, CF 3CO2H, CF3SO3/sub

Nickel-catalyzed efficient and practical Suzuki-Miyaura coupling of alkenyl and aryl carbamates with aryl boroxines

(Figure Presented) Suzuki-Miyaura coupling of unactivated alkenyl carbamates Is described to construct polysubstituted olefins. The developed process is also suitable for heteroaromatic and even electron-rich aromatic carbamates.

Infrared Spectra and Transmission of Electronic Effects in Substituted Phenyl N,N-Dimethylcarbamates and S-Phenyl N,N-Dimethylthiocarbamates

Carbonyl stretching frequencies in CCl4 and CHCl3 and hydroxyl stretching frequency shifts of phenol as a proton donor in CCl4 were measured for series of substituted phenyl N,N-dimethylcarbamates (I) and S-phenyl N,N-dimethylthiocarbamates (II).The data