614-17-5Relevant articles and documents
Photocatalysis in Aqueous Micellar Media Enables Divergent C-H Arylation and N-Dealkylation of Benzamides
Cybularczyk-Cecotka, Martyna,Predygier, J?drzej,Crespi, Stefano,Szczepanik, Joanna,Giedyk, MacIej
, p. 3543 - 3549 (2022/03/27)
Photocatalysis in aqueous micellar media has recently opened wide avenues to activate strong carbon-halide bonds. So far, however, it has mainly explored strongly reducing conditions, restricting the available chemical space to radical or anionic reactivity. Here, we demonstrate a controllable, photocatalytic strategy that channels the reaction of chlorinated benzamides via either a radical or a cationic pathway, enabling a chemodivergent C-H arylation or N-dealkylation. The catalytic system operates under mild conditions with methylene blue as a photocatalyst and blue LEDs as the light source. Factors determining the reactivity of substrates, their selectivity, and preliminary mechanistic studies are presented.
Hydrogenation of Secondary Amides using Phosphane Oxide and Frustrated Lewis Pair Catalysis
Bursch, Markus,Grimme, Stefan,K?ring, Laura,Paradies, Jan,Sitte, Nikolai A.
supporting information, p. 14179 - 14183 (2021/09/03)
The metal-free catalytic hydrogenation of secondary carboxylic acid amides is developed. The reduction is realized by two new catalytic reactions. First, the amide is converted into the imidoyl chloride by triphosgene (CO(OCCl3)2) using novel phosphorus(V) catalysts. Second, the in situ generated imidoyl chlorides are hydrogenated in high yields by an FLP-catalyst. Mechanistic and quantum mechanical calculations support an autoinduced catalytic cycle for the hydrogenation with chloride acting as unusual Lewis base for FLP-mediated H2-activation.
Amide bond formation in aqueous solution: Direct coupling of metal carboxylate salts with ammonium salts at room temperature
Nielsen, John,Tung, Truong Thanh
supporting information, p. 10073 - 10080 (2021/12/10)
Herein, we report a green, expeditious, and practically simple protocol for direct coupling of carboxylate salts and ammonium salts under ACN/H2O conditions at room temperature without the addition of tertiary amine bases. The water-soluble coupling reagent EDC·HCl is a key component in the reaction. The reaction runs smoothly with unsubstituted/substituted ammonium salts and provides a clean product without column chromatography. Our reaction tolerates both carboxylate (which are unstable in other forms) and amine salts (which are unstable/volatile when present in free form). We believe that the reported method could be used as an alternative and suitable method at the laboratory and industrial scales. This journal is
