Copper-catalyzed, N-auxiliary group-controlled switchable transannulation/nitration initiated by nitro radicals: selective synthesis of pyridoquinazolones and 3-nitroindoles was written by Shoberu, Adedamola;Li, Cheng-Kun;Qian, Hai-Feng;Zou, Jian-Ping. And the article was included in Organic Chemistry Frontiers in 2021.Reference of 175205-82-0 This article mentions the following:
Herein, a strategy based on the judicious choice of N-auxiliaries, which stabilize the substrates as well as allow precise and predictable control over their reactivity with tert-Bu nitrite was described. Thus, the stage was set for the copper-assisted, controllable synthesis of pyridoquinazolones or 3-nitroindoles. Mechanistic studies implicate a switch in the mechanism, in which N-2-pyridylindoles reacted via a nitrosation/transannulation process and N-2-pyridoylindoles underwent an amide bond dissociation/nitration sequence. Notably, the subsequent removal of the auxiliary groups was not required in these reactions. In the experiment, the researchers used many compounds, for example, 2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0Reference of 175205-82-0).
2-Bromo-3-(trifluoromethyl)pyridine (cas: 175205-82-0) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Reference of 175205-82-0