New methods for organic synthesis: visible light-mediated o-arylation of arenes via C-H activation

Abstract

New methodologies involving the activation of inert C(sp2)-H bonds have provided an alternative and efficient way for arylations of arenes. In the past decade, a lot of advances on direct arylations have emerged in the context of Ru catalysis. However, the vast majority of these reports require elevated temperatures (80-120 °C). To this end, we present a regioselective method for o-functionalisation of N-heteroaryl arenes at room temperature with a Ru(ΙΙ) catalyst, induced by visible light. A variety of electron-withdrawing and electron-donating groups are compatible with this process. Preliminary mechanistic experiments point towards a mechanism that could involve visible-light mediated η6-arene decomplexation followed by cyclometalation and oxidative addition of an aryl halide to the Ru centre.

Date of Award	1 Aug 2020
Original language	English
Awarding Institution	The University of Manchester
Supervisor	Michael Greaney (Supervisor) & Igor Larrosa (Supervisor)