73513-53-8Relevant academic research and scientific papers
Carbonylative Suzuki-Miyaura couplings of sterically hindered aryl halides: Synthesis of 2-aroylbenzoate derivatives
Bayer, Annette,Ismael, Aya,Skrydstrup, Troels
supporting information, p. 1754 - 1759 (2020/03/17)
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.
One-pot esterification and Ritter reaction: Chemo- and regioselectivity from tert-butyl methyl ether
Dawar, Pankaj,Bhagavan Raju,Ramakrishna, Ramesha A.
supporting information; experimental part, p. 4262 - 4265 (2011/08/21)
tert-Butyl methyl ether (TBME) has been effectively used as a reagent for esterification of carboxylic acids. By varying amounts of sulfuric acid, a remarkable regioselectivity in esterification has been demonstrated. Additionally, under the present reaction conditions, one-pot esterification and Ritter reaction are achieved in almost quantitative yield.
