42228-16-0Relevant articles and documents
Rapid Organocatalytic Formation of Carbon Monoxide: Application towards Carbonylative Cross Couplings
Zoller, Ben,Zapp, Josef,Huy, Peter H.
supporting information, p. 9632 - 9638 (2020/07/13)
Herein, the first organocatalytic method for the transformation of non-derivatized formic acid into carbon monoxide (CO) is introduced. Formylpyrrolidine (FPyr) and trichlorotriazine (TCT), which is a cost-efficient commodity chemical, enable this decarbonylation. Utilization of dimethylformamide (DMF) as solvent and catalyst even allows for a rapid CO generation at room temperature. Application towards four different carbonylative cross coupling protocols demonstrates the high synthetic utility and versatility of the new approach. Remarkably, this also comprehends a carbonylative Sonogashira reaction at room temperature employing intrinsically difficult electron-deficient aryl iodides. Commercial 13C-enriched formic acid facilitates the production of radiolabeled compounds as exemplified by the pharmaceutical Moclobemide. Finally, comparative experiments verified that the present method is highly superior to other protocols for the activation of carboxylic acids.
Synthesis of 4-(Dibromomethyl)benzaldehyde by Catalytic Debromophosphoryl- and Phosphonyloxylation of 1,4-Bis(dibromomethyl)benzene with Phosphorus(IV) Acid Methyl Esters and Its Properties
Gazizov,Ivanova, S. Yu.,Khairullin,Kirillina, Yu. S.,Gazizova
, p. 2243 - 2250 (2019/01/04)
A new procedure has been developed for the simultaneous preparation of terephthalaldehyde and 4-(dibromomethyl)benzaldehyde by catalytic debromophosphoryl- and phosphonyloxylation of 1,4-bis- (dibromomethyl)benzene with P(IV) acid methyl esters. The reaction of 4-(dibromomethyl)benzaldehyde with ortho esters in the presence of sulfuric acid gave the corresponding acetals, whereas in the presence of ZnCl2 terephthalaldehyde bis-acetals were formed. 4-(Dibromomethyl)benzaldehyde and its acetal were converted to methyl 4-(dibromomethyl)- and 4-(dimethoxymethyl)benzoates which were phosphorylated by the action of chlorophosphines, as well as by successive treatment with phosphorus(III) chloride and P(III) esters.
Synthesis of aromatic aldehyde acetals from (dibromomethyl)arenes
Gazizov,Ivanova, S. Yu.,Bashkirtseva, N. Yu.,Khairullina,Khairullin,Gazizova
, p. 1230 - 1233 (2017/12/02)
Zinc chloride-catalyzed double debromoalkoxylation of (dibromomethyl)arenes on treatment with trialkyl orthoformates resulted in the corresponding aromatic aldehyde acetals. On the first step, α-brominated ether is formed, which undergoes the second debro