The Truce–Smiles rearrangement is a powerful method for functionalizing aromatic compounds, enabling the synthesis of various (hetero)aromatic groups. This work summarizes recent advancements in this area.
A practical electrochemical sulfonylation-triggered Truce–Smiles rearrangement of N-allylbenzamides yielded sulfone- and sulfonic acid-containing β-arylethylamines under mild and oxidant-free reaction conditions.
A novel visible-light-induced photoredox platform for general Truce–Smiles rearrangement of N-sulfinyl acrylamides with aqueous sulfoxonium ylides as carbon radical precursors.
A photoredox-catalyzed alkylarylation of activated alkenes via a ring-opening/Truce–Smiles rearrangement cascade is developed. The protocol features broad substrate scope and excellent functional group compatibility.
The first highly regioselective tandem indole formation/Truce–Smiles rearrangement controlled by choice of ligands for K+ is presented. Use of N,N-diethylethylenediamine gives 2,3-disubstituted indoles whereas 18-crown-6 gives benzhydryl indoles.