title: Scope of Successive C-H Functionalizations of the Methyl Group in 3-Picolines: Intramolecular Carbonylation of Arenes to the Metal-Free Synthesis of 4-Azafluorenones.
abstract: A transition-metal-free, t-BuOOH mediated intramolecular carbonylation of arenes in 2-aryl-3-picolines via oxidative C-H functionalizations of the methyl group has been developed, providing an expedient synthesis of 4-azafluorenones. Distinct from the current literature wherein methylarenes have been used as acylating agents, 2-aryl-3-picolines in this study are transformed into aldehydes, which give 4-azafluorenones upon rapid intramolecular acylation. The study demonstrates the first example of intramolecular carbonylation of arenes utilizing a methyl group as latent carbonyl functionality.
authors.affiliation: Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research , S. A. S. Nagar, Punjab 160062, India.
authors.forename: Joydev K
authors.initials: JK
authors.lastname: Laha
authors.affiliation: Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research , S. A. S. Nagar, Punjab 160062, India.
authors.forename: Krupal P
authors.initials: KP
authors.lastname: Jethava
authors.affiliation: Department of Pharmaceutical Technology (Process Chemistry), National Institute of Pharmaceutical Education and Research , S. A. S. Nagar, Punjab 160062, India.
authors.forename: Sagarkumar
authors.initials: S
authors.lastname: Patel