Accessible, Direct Photochemical Route for the Amine-Free Synthesis of Azoxybenzene and Functional Azoxy Derivatives via Nitroarene Homocoupling
- Date
- August 16, 2022
- Time
- 1:00 PM EDT - 4:00 PM EDT
- Location
- Virtual Zoom
- Open To
- Event open to Students, Faculty, Staff, Post-Doctoral Fellows, Public
- Contact
- Sarah Kovacs skovacs@torontomu.ca
Candidate: Ali Yaghoubian
Supervisor: Dr. Stefania Impellizzeri and Dr. Marc Adler
ABSTRACT
In this body of work I report on a direct photochemical method for the one-pot synthesis of azoxybenzene and substituted azoxy derivatives from nitrobenzene building blocks. Using this approach, a 100% conversion efficiency of nitrobenzene and 93% yield of azoxybenzene was achieved. This protocol can be replicated at room temperature and under air, without the assistance of additional catalysts or reagents, and can be applied to substrates with a wide range of substituent groups. A family of porphyrin silane compounds were also studied as potential photocatalysts to facilitate the reduction of nitrobenzene to aniline. Although a 90% conversion efficiency of nitrobenzene and 32% yield of aniline was achieved, observed degradation of the catalysts limit potential application of this system.
