Palladium‐Catalyzed Efficient Synthesis of Benzofuro[3,2‐b]Pyrroles and Pyrrolo[3,2‐b]Indoles: Access to Nitrilo Substituted Benzofuro[3,2‐b]Indoles and Indolo[3,2‐b]Indoles Using DDQ
Year: 2025
Type: article
Abstract: We report an elegant method for the construction of fused pyrrole rings via palladium-catalyzed reactions of aryl iodides with N-prop-2-ynylated 3-aminobenzofurans/3-aminoindoles leading to the general synthesis of benzofuro[3,2-b]pyrroles/pyrrolo[3,2-b]indoles via 3-(arylidene)-2,3-dihydro intermediates. Exposing the intermediates to 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) delivered benzofuro[3,2-b]indoles (BFIs) and indolo[3,2-b]indoles (IIs) containing vicinal cyano groups. These transformations constitute a rapid intermolecular assembly through several carbon - carbon bond forming reactions, involving a single electron transfer (SET) process in the crucial steps. Photophysical studies of selected products identified promising candidates for future applications.
Source: Chemistry - A European Journal
Authors: Raghunath Das, Debasmita Mondal, Sarat Chatterjee, Chinmay Chowdhury
Institution: Indian Institute of Chemical Biology
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W4409670675