Palladium-Catalyzed Annulation of Diarylamines with Olefins through C-H Activation: Direct Access to N-Arylindoles was written by Sharma, Upendra;Kancherla, Rajesh;Naveen, Togati;Agasti, Soumitra;Maiti, Debabrata. And the article was included in Angewandte Chemie, International Edition in 2014.Computed Properties of C14H12N2O The following contents are mentioned in the article:
A palladium-catalyzed dehydrogenative coupling between diarylamines and olefins has been discovered for the synthesis of substituted indoles. This intermol. annulation approach incorporates readily available olefins for the first time and obviates the need of any addnl. directing group. An ortho palladation, olefin coordination, and β-migratory insertion sequence has been proposed for the generation of olefinated intermediate, which is found to produce the expected indole moiety. This study involved multiple reactions and reactants, such as 4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1Computed Properties of C14H12N2O).
4-((4-Methoxyphenyl)amino)benzonitrile (cas: 319016-04-1) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Computed Properties of C14H12N2O
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts