234449-91-3Relevant articles and documents
Palladium-catalyzed carbonylation of aryl bromides using microwave heating and bis[CP-Fe(II)-(CO)2] as a carbon monoxide source
Roy, Tamal,Rydfjord, Jonas,S?vmarker, Jonas,Nordeman, Patrik
, p. 1230 - 1232 (2018)
A palladium-catalyzed, microwave assisted carbonylative reaction is described for the synthesis of benzamides from aryl bromides and primary or secondary amines. The developed method uses bis(cyclopentadienyldicarbonyliron) as a solid source of carbon monoxide to produce a diverse set of secondary and tertiary amides in 42–82% yield.
Carboxyboronate as a Versatile In Situ CO Surrogate in Palladium-Catalyzed Carbonylative Transformations
Tien, Chieh-Hung,Trofimova, Alina,Holownia, Aleksandra,Kwak, Branden S.,Larson, Reed T.,Yudin, Andrei K.
supporting information, p. 4342 - 4349 (2020/12/25)
The application of carboxy-MIDA-boronate (MIDA=N-methyliminodiacetic acid) as an in situ CO surrogate for various palladium-catalyzed transformations is described. Carboxy-MIDA-boronate was previously shown to be a bench-stable boron-containing building block for the synthesis of borylated heterocycles. The present study demonstrates that, in addition to its utility as a precursor to heterocycle synthesis, carboxy-MIDA-boronate is an excellent in situ CO surrogate that is tolerant of reactive functionalities such as amines, alcohols, and carbon-based nucleophiles. Its wide functional-group compatibility is highlighted in the palladium-catalyzed aminocarbonylation, alkoxycarbonylation, carbonylative Sonogashira coupling, and carbonylative Suzuki–Miyaura coupling of aryl halides. A variety of amides, esters, (hetero)aromatic ynones, and bis(hetero)aryl ketones were synthesized in good-to-excellent yields in a one-pot fashion.
Application of phase-vanishing method with CO gas evolution to carbonylation reactions
Adachi, Yusuke,Matsubara, Hiroshi
, p. 89 - 95 (2018/10/26)
Although carbon monoxide (CO) is considered a practical source of the carbonyl functionality in various compounds, handling CO gas is difficult. The phase-vanishing (PV) method, using highly fluorinated solvents as the phase screen, was thus employed, in which CO was evolved for use in organic synthesis. An H-shaped reactor bearing two reaction chambers was employed. In the first chamber, CO was efficiently generated from sulfuric acid and ammonium formate under the PV conditions, and then consumed in the second chamber in a range of palladium-catalysed carbonylation reactions, affording the desired products. Use of this PV system allowed for easy and safe generation of hazardous CO gas, and its use thereof in organic synthesis.
