Work

Palladium-catalyzed regioselective C1-selective nitration of carbazoles

Year: 2025

Type: article

Abstract: Carbazoles are ubiquitous and privileged heterocyclic scaffolds in various functional organic materials and naturally occurring products. Although extensive efforts have focused on developing synthetic strategies toward carbazole derivatives, direct regioselective functionalization of the carbazole core remains challenging due to the inherently higher reactivity at the C3/C6 positions. In this study, we report a palladium-catalyzed, directing group-assisted, regioselective C1-H nitration of carbazoles. The protocol features a removable directing group and is amenable to gram-scale synthesis. This strategy provides a valuable platform for the selective functionalization of carbazoles, offering potential applications in optoelectronics, functional organic materials, and related areas while contributing to the advancement of C-H activation methodologies.

Source: Beilstein Journal of Organic Chemistry

DOI: 10.3762/bjoc.21.190

Authors: Vikash Kumar, Jyothis Dharaniyedath, Aiswarya T P, Sk Ariyan, Chitrothu Venkatesh, Parthasarathy Gandeepan

Institution: Indian Institute of Technology Tirupati

Language: English

Topic: Catalytic C–H Functionalization Methods

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

Funders: Arthritis National Research Foundation, National Research Foundation, Ministry of Education, India

Award: G3940417575