Cascade Approach to Highly Functionalized Biaryls by a Nucleophilic Aromatic Substitution with Arylhydroxylamines was written by Guo, Lirong;Liu, Fengting;Wang, Liying;Yuan, Hairui;Feng, Lei;Kurti, Laszlo;Gao, Hongyin. And the article was included in Organic Letters in 2019.Application In Synthesis of 6-Fluoropicolinonitrile This article mentions the following:
A transition-metal free synthesis of highly functionalized 2-hydroxy-2′-amino-1,1′-biaryls from N-arylhydroxylamines has been developed. This operationally simple and readily scalable approach relies on a cascade of reactions that initially generates transient N,O-diarylhydroxylamines, via direct O-arylation, which then undergo rapid [3,3]-sigmatropic rearrangement and subsequent rearomatization to form NOBIN-type products, e.g., I. These structurally diverse functionalized biaryls are obtained under mild conditions in good to excellent isolated yields. In the experiment, the researchers used many compounds, for example, 6-Fluoropicolinonitrile (cas: 3939-15-9Application In Synthesis of 6-Fluoropicolinonitrile).
6-Fluoropicolinonitrile (cas: 3939-15-9) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Application In Synthesis of 6-Fluoropicolinonitrile