6683-58-5

Upstream product

• 7199-41-9 Isosequirin-trimethylether; 1-p-Methoxyphenyl-3-α,β-dihydroxyethyl-5,6-dimethoxy-indan 
• 201230-82-2 carbon monoxide 
• 17667-32-2 methyl 6-bromo-3,4-dimethoxybenzoate 
• 5720-07-0 4-methoxyphenylboronic acid 
• 186581-53-3 diazomethane 
• 6683-57-4 4,5-Dimethoxy-2-(4-methoxy-benzoyl)-benzoic acid 
• 4821-94-7 4,5-dimethoxyphthalic anhydride 
• 100-66-3 methoxybenzene 

Downstream Products

• 6683-59-6 6,7-dimethoxy-4-(4-methoxy-phenyl)-benzo[d][1,2]oxazin-1-one 

Relevant academic research and scientific papers

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.