2267-95-0Relevant academic research and scientific papers
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.).
Cu-catalyzed arylation of bromo-difluoro-acetamides by aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts: New entries to aromatic amides
Iaroshenko, Viktor O.,Jakubczyk, Micha?,Lanka, Suneel,Mkrtchyan, Satenik,Pittelkow, Michael
, (2021/06/12)
We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2, 2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl precursors such as aryl boronic acids, aryl trialkoxysilanes and dimethyl-aryl-sulfonium salts were used as the source for the aryl substituents. The scope of the reactions was tested, and the reactions were insensitive to the electronic nature of the aryl groups, as both electron-rich and electron-deficient aryls were successfully introduced. A wide range of 2-bromo-2, 2-difluoroacetamides as either aliphatic or aromatic secondary or tertiary amides were also reactive under the developed conditions. The described synthetic protocols displayed excellent efficiency and were successfully utilized for the expeditious preparation of diverse aromatic amides in good-to-excellent yields. The reactions were scaled up to gram quantities.
Oxidative Amidation of Amines in Tandem with Transamidation: A Route to Amides Using Visible-Light Energy
Nandi, Jyoti,Vaughan, Matthew Z.,Sandoval, Arturo León,Paolillo, Joshua M.,Leadbeater, Nicholas E.
, p. 9219 - 9229 (2020/08/14)
A methodology is reported for preparing amides using amines as an acyl source. The protocol involves the visible-light-promoted oxidative amidation of amines with pyrazole to synthesize N-acyl pyrazoles followed by transamidation. By combining photoredox catalysis with oxoammonium cations in the presence of sodium persulfate as a terminal oxidant, the N-acyl pyrazoles could be prepared efficiently and effectively using blue LEDs. The transamidation step was performed without the need to purify the N-acyl pyrazole intermediate, and a range of amides were generated in good to excellent yields.
Nickel-catalyzed reductive amidation of aryl-triazine ethers
Heravi, Majid M.,Panahi, Farhad,Iranpoor, Nasser
supporting information, p. 1992 - 1995 (2020/02/22)
The reaction of activated phenolic compounds, 2,4,6-triaryloxy-1,3,5-triazine (aryl-triazine ethers), with various isocyanates or carbodiimides in the presence of a nickel pre-catalyst resulted in the synthesis of aryl amides in good to excellent yields.
Base-Promoted Chemodivergent Formation of 1,4-Benzoxazepin-5(4H)-ones and 1,3-Benzoxazin-4(4H)-ones Switched by Solvents
Chen, Qian,Wang, Yunpeng,Hua, Ruimao
supporting information, (2019/11/02)
The KOH-promoted chemodivergent benzannulation of ortho-fluorobenzamides with 2-propyn-1-ol can afford either 1,4-benzoxazepin-5(4H)-ones or 1,3-benzoxazin-4(4H)-ones in good yields with high selectivity, depending greatly upon the use of solvents. In the
Tert -Butyl nitrite promoted transamidation of secondary amides under metal and catalyst free conditions
Sureshbabu, Popuri,Azeez, Sadaf,Chaudhary, Priyanka,Kandasamy, Jeyakumar
supporting information, p. 845 - 850 (2019/01/30)
A mild and efficient method is demonstrated for the transamidation of secondary amides with various amines including primary, secondary, cyclic and acyclic amines in the presence of tert-butyl nitrite. The reaction proceeds through the N-nitrosamide intermediate and provides the transamidation products in good to excellent yields at room temperature. Moreover, the developed methodology does not require any catalyst or additives.
Nitrate-promoted Selective C-H Fluorination of Benzamides and Benzeneacetamides
Ning, Xing-Qian,Lou, Shao-Jie,Mao, Yang-Jie,Xu, Zhen-Yuan,Xu, Dan-Qian
supporting information, p. 2445 - 2448 (2018/04/27)
A versatile and site-selective nitrate-promoted C-H bond fluorination using various weak coordinating amides as intrinsic directing groups was developed. Diverse tertiary and secondary amides underwent selective aromatic C-H bond fluorination, which featu
