The diazo quinone or quinone diazide compounds have been extensively utilized to introduce phenol/naphthol moieties into hydrocarbons or nitrogen-containing heterocycles under transition metal catalysis [1].

The reactions proceed via C–H/X-H insertion or migratory insertion of metal carbenes. In this presentation, the racemic synthesis of important ligand like 8-azaBINOL and phosphine ligands like QUINAP, METHOX, PINAP, PHENAP will be discussed [2,3]. Construction of indolocoumarin, especially isolamellarins, using the migratory insertion of quinoid carbene will be explained [4]. A straightforward Rh(III)-catalyzed method for the introduction of naphthol/phenol moieties to the C(sp3)–H bond of 8-methylquinoline using diazonaphthalen-2(1H)-ones/quinone diazides will be explained [5].

Further, site-selective N-arylation of benzotriazole, 2-hydroxy pyridine and amide bonds using quinoid carbene via insertion and migratory insertion methods will be explored [6-8]. Next, a Ru(II)-catalyzed method to construct O-alkylated arylnaphthyl thioether derivatives using α-thioesters and diazonaphthoquinone via an unprecedented [1,4]-oxa sigmatropic rearrangement and in a complementary method, O-heteroaryl alkylnaphthyl thioether derivatives via a a concerted intramolecular SNAr-type reaction will be explained [9].