Radical Truce-Smiles Rearrangements In Organic Synthesis

Abstract

The use of mild reducing agents for the initiation of Radical-Smiles rearrangements using readily available ortho-(arylsulfonyl)oxy)aryldiazonium tetrafluoroborates as precursors is of particular relevance to the synthesis of bi-aryl compounds under metal-free, environmentally benign, reaction conditions. This project describes the optimization of Radical Smiles rearrangements for the synthesis of bi-aryls using readily available reducing agents in the initiation phase of the reaction. During this process optimization we discovered that rongalite, a mild reducing agent that is available on an industrial scale, could be utilized in place of more commonly used, but potentially more hazardous, reagents (e.g. TiCl3, n-Bu3SnH), for the promotion of these reactions. The scope and limitations of this variant of the radical Smiles rearrangement is discussed.

Date of Award	1 Aug 2023
Original language	English
Awarding Institution	The University of Manchester
Supervisor	Peter Quayle (Supervisor) & Roger Whitehead (Supervisor)