873548-66-4Relevant 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.
A convenient access to thienyl-substituted phthalazines
Raposo, M. Manuela M.,Sampaio, Ana M. B. A.,Kirsch
, p. 1245 - 1251 (2007/10/03)
A synthesis of 1-alkoxy- and 1-amino- substituted 4-(2-thienyl)- phthalazines is described from halo-derivatives of 4-(2-thienyl)-1-(2H)- phthalazinone 3.
