Two-dimensionally extended, polycyclic heteroaromatic molecules (heterocyclic nanographenes) are a highly versatile class of organic materials, applicable as functional chromophores and organic semiconductors. In this Review, we discuss the rich chemistry of large heteroaromatics, focusing on their synthesis, electronic properties, and applications in materials science. This Review summarizes the historical development and current state of the art in this rapidly expanding field of research, which has become one of the key exploration areas of modern heterocyclic chemistry.

Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds: Synthetic Routes, Properties, and Applications

Mild, efficient, copper-catalyzed N-arylation procedures for nitrogen heterocycles, amides, carbamates, and C-arylation procedures for malonic acid derivatives have been developed that afford high yields of arylated products with excellent selectivity. The N-arylation of imidazole with aryl bromides or iodides was found to be greatly accelerated by inexpensive, air-stable catalyst systems, combining catalytic copper salts or oxides with a set of structurally simple chelating ligands. The reaction was shown to be compatible with a broad range of aryl halides, encompassing sterically hindered, electron-poor, and electron-rich ones, providing the arylated products under particularly mild conditions (50-82 degrees C). The lower limit in ligand and catalyst loading and the scope of Ullmann-type condensations catalyzed by complexes bearing those ligands with respect to the nucleophile class have also been investigated. Chelating Schiff base Chxn-Py-Al (1c) generates a remarkably general copper catalyst for N-arylation of pyrrole, indole, 1,2,4-triazole, amides, and carbamates; and C-arylation of diethyl malonate, ethyl cyanoacetate, and malononitrile with aryl iodides under mild conditions (50-82 degrees C). The new method reported here is the most successful to date with regard to Ullmann-type arylation of some of these nucleophiles.

https://onlinelibrary.wiley.com/doi/pdf/10.1002/chem.200400582

Highly efficient and mild copper-catalyzed N- and C-arylations with aryl bromides and iodides.

An efficient and convenient synthesis of optically active cycloalkanols by utilizing the chiral cationic palladium complex as the catalyst was achieved in mild conditions with high yield and high enantioselectivity.

Cationic palladium complex catalyzed highly enantioselective intramolecular addition of arylboronic acids to ketones. A convenient synthesis of optically active cycloalkanols.

Methods published over the last 10 years for the production of substituted 1(2H)-isoquinolones, including those involving the use of organometallic compounds, are discussed.

Indira Datta

Papers

Studies on oxygen heterocycles: Part-1: Acid catalysed and photochemical reactions of some aryldiazoketones

Studies on enamides Part-21:A novel photochemical synthesis of 9H-indolo [3,2,1-de] phenanthridin-9-one, a benzcanthine analogue

Studies on enamides. part-41 : photochemical investigations of n-aroyldiphenylamines

Diazo Transfer Reaction in Solid State

Studies on enamides. Part-3 : A novel photochemical synthesis of 9-arylacridines☆