104847-07-6Relevant articles and documents
Amberlyst-15 as a recyclable heterogeneous catalyst for synthesis of N-tert-butylamides via Ritter-type reaction
Mokhtary, Masoud,Goodarzi, Gholamreza
, p. 293 - 296 (2012)
Highly efficient method for the preparation of N-tert-butylamides by reaction of nitriles with tert-butylacetate is described using Amberlyst-15 as a recyclable heterogeneous catalyst. Selective amidation of benzonitrile in the presence of acetonitrile was also achieved.
Highly efficient microwave-assisted CO aminocarbonylation with a recyclable Pd(II)/TPP-β-cyclodextrin cross-linked catalyst
Calcio Gaudino, Emanuela,Carnaroglio, Diego,Martina, Katia,Palmisano, Giovanni,Penoni, Andrea,Cravotto, Giancarlo
, p. 499 - 505 (2015)
The incorporation of the carbonyl moiety into organic molecules using a three-component matrix, including carbon monoxide, an organic halide, and a nucleophilic component, offers a simple and versatile approach to the formation of carboxylic acids, anhydrides, esters, amides, and ketones. The design of a sustainable synthetic protocol for aminocarbonylation can be efficiently accomplished using a multifaceted strategy that combines solid green catalysts and suitable enabling techniques. The safe and synergistic use of carbon monoxide in a microwave reactor under pressure may be able to create a technological breakthrough in aminocarbonylation reactions. Moreover, a new recyclable catalytic system "CβCAT" based on Pd(II)-triphenylphosphine embedded in cross-linked β-cyclodextrin (hexamethylene diisocyanate) has been found to be very efficient in aryl iodide aminocarbonylation reactions.
Bu4NI-Catalyzed Oxygen-Centered Radical Addition between Acyl Peroxides and Isocyanides
Chen, Meng,Li, Yang,Tang, Hong,Ding, Hao,Wang, Kai,Yang, Lingen,Li, Cuiting,Gao, Meng,Lei, Aiwen
, p. 3147 - 3150 (2017)
A novel oxygen-centered radical addition between acyl peroxides and isocyanides has been developed. A diverse collection of valuable arylcarboxyamides were easily synthesized by this protocol. From the preliminary mechanistic study, the elimination of carbon dioxide affords the product via an intramolecular rearrangement.
Increasing rates and scope of reactions: Sluggish amines in microwave-heated aminocarbonylation reactions under air
Wannberg, Johan,Larhed, Mats
, p. 5750 - 5753 (2003)
Commercially available molybdenum hexacarbonyl serves as a convenient and solid carbon monoxide source in palladium-catalyzed aminocarbonylations of aryl bromides and iodides. This improved microwave protocol, relying on DBU as base and THF as solvent, enables rapid couplings using otherwise sluggish anilines, tert-butylamine, and free amino acids. In addition, Cr(CO)6 and W(CO)6 were found to be useful alternative CO-releasing reagents. Altogether, 16 different aromatic amides were synthesized under air in 35-95% yield after only 15 min of controlled microwave irradiation.
A Comparison of Immobilised Triphenylphosphine and 1-Hydroxybenzotriazole as Mediators of Catch-and-Release Acylation Under Flow Conditions
Aldrich-Wright, Janice R.,Dankers, Christian,Gordon, Christopher P.,Jurisinec, Ashley,Menti-Platten, Maria,Tadros, Joseph
supporting information, (2022/03/07)
Described herein is a comparative study of immobilised triphenylphosphine (PS-PPh3) and 1-hydroxybenzotriazole (PS-HOBt) to mediate amide couplings under continuous flow. Compared to Appel-type amidations (PS-PPh3), the developed ‘catch-and-release’ approach (PS-HOBt) afforded near-quantitative amide conversions. Utilising this strategy, sulfonyl chloride amenability enabled facile access to an expanded library of sulfonate and sulfonamides. Post-constructional peptide modification was also demonstrated, affording two Nβ-functionalised pentapeptides in high yields and purities. In contrast to frequently utilised coupling agents, the PS-HOBt resin could be recycled six times without a reduction in efficacy or regeneration requirements.
Copper-Catalyzed N-Directed Distal C(sp3)-H Sulfonylation and Thiolation with Sulfinate Salts
Chen, Guang-Le,He, Shi-Hui,Cheng, Liang,Liu, Feng
supporting information, p. 8338 - 8342 (2021/10/25)
We herein report a selective and catalytic C(sp3)-H functionalization approach to access amines bearing organo-sulfonyl and organo-thiol groups. This reaction proceeds through a cascade process of N-radical formation, alkyl radical formation via 1,5-HAT, and C-S bond formation, thereby offering a series of functionalized amines. This method could enable primary, secondary, and tertiary C(sp3)-H sulfonylation and thiolation and also exhibits good functional group tolerance.
A convenient synthesis of N-tert-butyl amides by the reaction of di-tert-butyl dicarbonate and nitriles catalyzed by Cu(OTf)2
Chen, Junqing,Feng, Chengliang,Ji, Min,Tang, Yuqi,Yang, Wanfeng
, p. 602 - 608 (2020/04/27)
The utility of Cu(OTf)2 as the catalyst for the synthesis of a series of N-tert-butyl amides in excellent isolated yields via the reaction of nitriles (alkyl, aryl, benzyl, and furyl nitriles) with di-tert-butyl dicarbonate is described. Cu(OTf)2 is a highly stable and efficient catalyst for the present Ritter reaction under solvent-free conditions at room temperature.
