31558-46-0

Usage

InChI:InChI=1/C15H14O4/c1-17-13-9-7-12(8-10-13)11-18-15(16)19-14-5-3-2-4-6-14/h2-10H,11H2,1H3

Upstream product

• 1885-14-9 phenyl chloroformate 
• 105-13-5 4-Methoxybenzyl alcohol 

Downstream Products

• 18912-37-3 4-methoxybenzyl hydrazinecarboxylate 
• 19962-28-8 4-methoxybenzyl phenyl ether 
• 111371-54-1 1-(4-Methoxybenzyloxycarbonyl)-2-(5-methyl-2-picolylmercapto)-1H-thieno[3,4-d]imidazole 
• 946-80-5 (benzyloxy)benzene 
• 31574-11-5 4-chlorophenyl-(4-methoxyphenylmethyl) ether 
• 7700-27-8 4-chlorophenyl benzyl ether 
• 1358795-44-4 4-methoxybenzyl 2-(dimethylamino)ethylcarbamate 
• 287729-67-3 bis((4-methoxyphenyl)methyl) carbonate 
• 1003-66-3 phenol-d1 
• 74384-21-7 phenyl 2-(4-(methoxy)phenyl)acetate 
• 23931-65-9 N,N'-Bis-(4-methoxy-benzyloxycarbonyl)-L-cystin 
• 42533-12-0 Z(OMe)-Lys(Z)-OH 
• 20890-95-3 p-methoxybenzyloxycarbonyl-Asp-OH 
• 23234-83-5 Z(OMe)-Leu-OH 

Relevant academic research and scientific papers

Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates: Direct Synthesis of Aryl 2-Arylacetates

A procedure on palladium-catalyzed decarboxylative alkoxycarbonylation of carbonates for the synthesis of aryl 2-arylacetates has been developed. A broad range of aryl 2-arylacetates were obtained in good yields under mild conditions under a carbon monoxide atmosphere. Interestingly, other alcohols can be added as nucleophiles as well, and the corresponding esters were also obtained in good yields.

Activation of Benzyl Aryl Carbonates: The Role of Cation-π Interactions

Benzyl aryl carbonates can react with a nucleophile to yield an activated electrophile and an aryloxide anion. Previously, we had utilized this in the synthesis of α-nitro esters from nitroalkanes. To further understand the process of activation of these carbonates by nucleophiles, we have performed kinetic studies on the hydrolysis of carbonates using nucleophiles. Rate constants for the hydrolysis were obtained under pseudo-first-order conditions with DABCO as the nucleophile. A comparison of rate constant for hydrolysis of isobutyl phenyl carbonate with benzyl phenyl carbonate shows that the presence of benzyl group results in a 16-fold acceleration of hydrolysis rate. This indicates that the transition state for activation of carbonate is stabilized by cation-π interactions. A comparison of the rate constant for various aromatic rings indicates that electron-donating substituents on the benzyl groups accelerate the rate of hydrolysis. Studies were also carried out with DMAP as nucleophile and the results are presented. Our studies show that stable carbonates can be activated using nucleophiles. Activated acyl groups generated from acid anhydrides have been used in several enantioselective reactions. Our studies show that carbonates can be stable alternatives to acid anhydrides.

Benzyl protection of phenols under neutral conditions: Palladium-catalyzed benzylations of phenols

Benzyl protection of phenols under neutral conditions was achieved by using a Pd(n3-C3H5)Cp-DPEphos catalyst. The palladium catalyst efficiently converted aryl benzyl carbonates into benzyl-protected phenols through the decarboxylative etherification. Alternatively, the nucleophilic substitution of benzyl methyl carbonates with phenols proceeded In the presence of the catalyst, yielding aryl benzyl ethers.