Work

The Vicinal‐Diiodination of the HDDA‐Benzynes by N ‐Iodo‐ succinimide (NIS) Through a Radical Pathway

Year: 2025

Type: article

Abstract: The 1,2-diradical reactivity of the HDDA-benzynes (thermal) has not been explored well in comparison to their ionic reactivity. Accordingly, the radical trapping reactions of these reactive intermediates are very scarce in literature. Herein, we report the iodine-radical trapping reaction of the HDDA-benzynes for the construction of structurally divergent vicinal-diiodo arenes. The N-iodosuccinimide (NIS) has been employed as the source of radical iodine under thermal heating conditions. The existence of the arene-radical intermediates and the radical mechanism has been supported by the EPR spectral analysis of the reaction mixture. Several fruitful control experiments suggested that the 4-iodination (mono-) of the HDDA-benzynes is faster than the 5-iodiniation. The process is general in terms of substituents on the diynes as well as the nature of the tethering units. To the best of our knowledge, this is the first report on the vicinal-diiodination as well as radical diiodination of HDDA-benzynes.

Source: Chemistry - A European Journal

DOI: 10.1002/chem.202500185

Authors: Siddique Khan, Beeraiah Baire

Institution: Indian Institute of Technology Madras

Language: English

Topic: Cyclization and Aryne Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: Department of Science and Technology, Ministry of Science and Technology, India, Indian Institute of Technology Madras, Science and Engineering Research Board

Award: G2766051461