A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups was written by Annapureddy, Rajasekar Reddy;Jandl, Christian;Bach, Thorsten. And the article was included in Journal of the American Chemical Society in 2020.Safety of 1-Hydroxyisoquinoline This article mentions the following:
A silver-catalyzed amination was reported that occurred at the aliphatic C3-substituent of various quinolones and pyridones. The C-H amination reaction proceeded with high site- and enantioselectivity (14 examples, 83-97% ee). The key to its success was the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahydro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol %) served as the silver source, PhI=NNs as the nitrene precursor and 1,10-phenanthroline as the co-ligand. The reaction outcome can be understood by assuming a nitrene C-H insertion within a hydrogen-bonded silver complex in which a single C-H bond was exposed to the catalytic reaction center. In the experiment, the researchers used many compounds, for example, 1-Hydroxyisoquinoline (cas: 491-30-5Safety of 1-Hydroxyisoquinoline).
1-Hydroxyisoquinoline (cas: 491-30-5) belongs to isoquinoline derivatives. Being an analog of pyridine, isoquinoline is a weak base, with a pKa of 5.14. The Pomeranz–Fritsch reaction provides a method for the preparation of isoquinoline. This reaction uses a benzaldehyde and aminoacetoaldehyde diethyl acetal, which in an acid medium react to form isoquinoline.Safety of 1-Hydroxyisoquinoline
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem