5449-71-8

Upstream product

• 201230-82-2 carbon monoxide 
• 17763-70-1 methyl 2-(trifluoromethylsulfonyloxy)benzoate 
• 70744-47-7 (p-methoxyphenyl)tri-n-butylstannane 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 79422-15-4 2-(4-methoxyphenyl)-1,3,6,2-dioxazaborocane 
• 5720-07-0 4-methoxyphenylboronic acid 
• 74-88-4 methyl iodide 
• 85-44-9 phthalic anhydride 
• 85-57-4 2-(4-hydroxy-benzoyl)-benzoic acid 

Downstream Products

• 57591-01-2 (2-(hydroxymethyl)phenyl)(4-methoxyphenyl)methanol 
• 855422-65-0 1,2-bis-(4-hydroxy-benzoyl)-benzene 
• 7477-30-7 1,2-bis-(α-hydroxyimino-4-methoxy-benzyl)-benzene 
• 21615-74-7 3-(4-methoxyphenyl)phthalide 
• 5441-28-1 1,4-bis-(4-methoxy-phenyl)-phthalazine 
• 1151-15-1 2-(4-methoxybenzoyl)benzoic acid 
• 7477-28-3 o-bis(p-methoxyphenoyl)benzene 

Relevant academic research and scientific papers

Construction of an isoquinolinone framework from carboxylic-ester-directed umpolung ring opening of methylenecyclopropanes

An interesting type of reaction involving functionalized methylenecyclopropanes (MCPs) has been revealed. Here, a nucleophilic attack of an anionic species onto a partially polarity-reversed MCP was realized by treating a neighbouring carboxylic ester tethered to the MCP and amine with KHMDS to realize an umpolung ring opening of the MCP. This work established an operationally convenient protocol for the rapid construction of isoquinolinone frameworks. This journal is

Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivatives

We have developed a carbonylative approach to the synthesis of diversely substituted 2-aroylbenzoate esters featuring a new protocol for the carbonylative coupling of aryl bromides with boronic acids and a new strategy to favour carbonylative over non-carbonylative reactions. Two different synthetic pathways-(i) the alkoxycarbonylation of 2-bromo benzophenones and (ii) the carbonylative Suzuki-Miyaura coupling of 2-bromobenzoate esters-were evaluated. The latter approach provided a broader substrate tolerance, and thus was the preferred pathway. We observed that 2-substituted aryl bromides were challenging substrates for carbonylative chemistry favouring the non-carbonylative pathway. However, we found that carbonylative Suzuki-Miyaura couplings can be improved by slow addition of the boronic acid, suppressing the unwanted direct Suzuki coupling and, thus increasing the yield of the carbonylative reaction.

Ruthenium-Catalyzed Enantioselective Hydrogenation/Lactonization of 2-Acylarylcarboxylates: Direct Access to Chiral 3-Substituted Phthalides

Highly enantioselective tandem hydrogenation/lactonization of various 2-acylarylcarboxylates including 2-aroylarylcarboxylates were realized by using [RuCl(benzene)(S)-SunPhos]Cl as the catalyst under mild reaction conditions. Excellent enantioselectivities (up to 99.6 % ee) and activities (S/C=1000) were obtained. This convenient and practical method enables a direct access to a series of highly optically pure 3-substituted phthalides that are very important molecules as valuable pharmacological compounds and diversified synthons for medicinal chemistry. Moreover, a gram-scale reaction was performed to further demonstrate the practicality of this approach.

Palladium-Catalyzed Environmentally Benign Acylation

Recent trends in research have gained an orientation toward developing efficient strategies using innocuous reagents. The earlier reported transition-metal-catalyzed carbonylations involved either toxic carbon monoxide (CO) gas as carbonylating agent or functional-group-assisted ortho sp2 C-H activation (i.e., ortho acylation) or carbonylation by activation of the carbonyl group (i.e., via the formation of enamines). Contradicting these methods, here we describe an environmentally benign process, [Pd]-catalyzed direct carbonylation starting from simple and commercially available iodo arenes and aldehydes, for the synthesis of a wide variety of ketones. Moreover, this method comprises direct coupling of iodoarenes with aldehydes without activation of the carbonyl and also without directing group assistance. Significantly, the strategy was successfully applied to the synthesis n-butylphthalide and pitofenone.

PROCESS FOR PRODUCING 4-PHENYL-4-OXO-2-BUTENOIC ESTER DERIVATIVE

A 4-phenyl-4-oxo-2-butenoate derivative is stably supplied in a short period of time, at low cost, in high purity and on an industrial scale by a process for producing the 4-phenyl-4-oxo-2-butenoate derivative, which comprises simultaneously or continuously reacting a sulfuric ester, an aromatic hydrocarbon and a maleic anhydride derivative.