Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine was written by Zhang, Deliang;Iwai, Tomohiro;Sawamura, Masaya. And the article was included in Organic Letters in 2020.Formula: C8H6N2O2 This article mentions the following:
In the presence of a catalyst generated from [Ir(cod)Cl]2 and the crosslinked polystyrene-bound diphosphine PS-DPPBz, indolines and selected partially saturated five- and six-membered nitrogen heterocycles underwent reversible acceptorless dehydrogenation to give aromatic nitrogen heterocycles. The method was used for the dehydrogenation of N-substituted indolines with various nitrogen substituents and substituents with various electronic and steric effects. Under 40 atm. of H2, indoles and a quinoline, isoquinoline, and quinoxaline underwent hydrogenation in the presence of the resin-bound iridium catalyst to yield partially saturated nitrogen heterocycles. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates. In the experiment, the researchers used many compounds, for example, 6-Nitro-1H-indole (cas: 4769-96-4Formula: C8H6N2O2).
6-Nitro-1H-indole (cas: 4769-96-4) belongs to indole derivatives. Indole exists overwhelmingly in the 1H-indole form as do other simple indoles. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.Formula: C8H6N2O2
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles