89399-21-3Relevant articles and documents
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.
Highly efficient preparation of amides from aminium carboxylates using N-(p-toluenesulfonyl) imidazole
Behrouz, Somayeh,Rad, Mohammad Navid Soltani,Forouhari, Elham
, p. 101 - 106 (2016/03/08)
Treatment of aminium carboxylates with N-(p-toluenesulfonyl)imidazole in the presence of triethylamine in DMF at 100 °C afforded the corresponding amides in good to excellent yields. N-(p-Toluenesulfonyl)imidazole proved to be a highly efficient coupling reagent for the preparation of numerous structurally diverse primary, secondary and tertiary amides.
Direct amide synthesis from equimolar amounts of carboxylic acid and amine catalyzed by mesoporous silica SBA-15
Tamura, Mizuki,Murase, Daisuke,Komura, Kenichi
supporting information, p. 769 - 776 (2015/03/14)
Direct amide synthesis from equimolar amounts of carboxylic acid and amine using mesoporous silica as a versatile heterogeneous catalyst is reported.