65492-63-9Relevant articles and documents
Mechanochemical Transformation of CF3 Group: Synthesis of Amides and Schiff Bases
Mkrtchyan, Satenik,Jakubczyk, Micha?,Lanka, Suneel,Yar, Muhammad,Ayub, Khurshid,Shkoor, Mohanad,Pittelkow, Michael,Iaroshenko, Viktor O.
supporting information, p. 5448 - 5460 (2021/10/19)
We communicate two mild, solvent-free mechanochemical coupling transformations of CF3 group with nitro compounds into amides or Schiff bases employing Ytterbia as a catalyst. This process proceeds via C?F bond activation, accompanied with utilisation of Si-based reductants/oxygen scavengers – reductants of the nitro group. The scope and limitations of the disclosed methodologies are thoroughly studied. To the best of our knowledge, this work is the first example of mechanical energy promoted transformation of the inert CF3 group into other functionalities. (Figure presented.).
Direct Amidation of Carboxylic Acids with Nitroarenes
Wang, Shao-Peng,Cheung, Chi Wai,Ma, Jun-An
, p. 13922 - 13934 (2019/11/03)
N-Aryl amides are an important class of compounds in pharmaceutical and agrochemical chemistry. Rapid and low-cost synthesis of N-aryl amides remains in high demand. Herein, we disclose an operationally simple process to access N-aryl amides directly from readily available nitroarenes and carboxylic acids as coupling substrates. This method involves the in situ activation of carboxylic acids to acyloxyphosphonium salt for one-pot amidation, without the need for isolation of the corresponding synthetic intermediates. Furthermore, the ease of preparation and workup allow the quick and efficient synthesis of a wide range of N-aryl amides, including several amide-based druglike and agrochemical molecules.
Transition metal free intramolecular selective oxidative C(sp3)-N coupling: Synthesis of N-aryl-isoindolinones from 2-alkylbenzamides
Verma, Ajay,Patel, Saket,Meenakshi,Kumar, Amit,Yadav, Abhimanyu,Kumar, Shailesh,Jana, Sadhan,Sharma, Shubham,Prasad, Ch. Durga,Kumar, Sangit
supporting information, p. 1371 - 1374 (2015/02/18)
A synthetic method has been developed for the preparation of biologically important isoindolinones including indoprofen and DWP205190 drugs from 2-alkylbenzamide substrates by transition metal-free intramolecular selective oxidative coupling of C(sp3)-H and N-H bonds utilizing iodine, potassium carbonate and di-tert-butyl peroxide in acetonitrile at 110-140 °C.