Yao, Wei published the artcilePhoto-induced C-H bond activation of N,N’-dialkylethylenediamine upon aza-Michael addition to 1,8-pyrenedione: facile synthesis of fluorescent pyrene derivatives, Application In Synthesis of 140-28-3, the publication is Organic Chemistry Frontiers (2018), 5(10), 1679-1683, database is CAplus.
Reaction between 1,8-pyrenedione and N,N’-dialkylethylenediamine to form highly fluorescent products, via aza-Michael addition followed by double C-H activation facilitated by visible light is discovered. Remarkably, the reaction intermediates and mono C-H bond activation product could only be formed when the reaction was carried out in the presence of a base and UV-light (254 nm). Dehydrogenation of the intermediate under room lighting converts it to the final products. The reaction is a general one as it works with a number of ethylenediamines with different substituents. The reaction mechanisms suggested that nucleophilic addition of the amine followed by dehydrogenation occurs to restore aromaticity and give an amine substituted 1,8-pyrenedione intermediate. The C-H activation requires photoexcitation via a radical mechanism. This work opens a new avenue for the construction of novel mols. with a pyrene core as a fluorophore with good quantum yields.
Organic Chemistry Frontiers published new progress about 140-28-3. 140-28-3 belongs to catalysis-chemistry, auxiliary class Benzenes, name is N1,N2-Dibenzylethane-1,2-diamine, and the molecular formula is C6H13NO2, Application In Synthesis of 140-28-3.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia