title: Open-Shell Phenalenyl in Transition Metal-Free Catalytic C-H Functionalization.
abstract: Open-shell phenalenyl chemistry has widely been explored in the last five decades demonstrating its potential in various applications including molecular switch, spin memory device, molecular battery, cathode material, etc. In this article, we have explored another new direction of open-shell phenalenyl chemistry toward transition metal-free catalytic C-H functionalization process. A phenalenyl ligand, namely, 9-methylamino-phenalen-1-one (4a), promoted chelation-assisted single electron transfer (SET) process, which facilitates the C-H functionalization of unactivated arenes to form the biaryl products. The present methodology offers a diverse substrate scope, which can be operated without employing any dry or inert conditions and under truly transition metal based catalyst like loading yet avoiding any expensive or toxic transition metal. This not only is the first report on the application of phenalenyl chemistry in C-H functionalization process but also provides a low-catalyst loading organocatalytic system (up to 0.5 mol % catalyst loading) as compared to the existing ones (mostly 20-40 mol %), which has taken advantage of long known phenalenyl based radical stability through the presence of its low-lying nonbonding molecular orbital.
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Rupankar
authors: R
authors: Paira
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Bhagat
authors: B
authors: Singh
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Pradip Kumar
authors: PK
authors: Hota
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Jasimuddin
authors: J
authors: Ahmed
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Samaresh Chandra
authors: SC
authors: Sau
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Justin P
authors: JP
authors: Johnpeter
authors: Department of Chemical Sciences, Indian Institute of Science Education and Research , Kolkata, Mohanpur-741246, India.
authors: Swadhin K
authors: SK
authors: Mandal