Enantioselective Ring-Opening of Cyclic Diaryliodoniums with 3-Hydroxy Benzo[d][1,2,3]triazin-4(3H)-ones: A 1,2-Difunctionalization Strategy

The catalytic asymmetric ring-opening of cyclic diaryliodoniums provides an efficient approach for constructing axial and point chiral molecules. However, previous methodologies have been limited to introducing only a single functional group at the ipso position of the C–I bond. Herein, we report the development of an enantioselective ring-opening reaction of cyclic diaryliodoniums with 3-hydroxybenzo[d][1,2,3]triazin-4(3H)-ones using newly developed chiral bipyridine ligands. This transformation is followed by a stereospecific [2,3]-sigmatropic rearrangement, thereby achieving unprecedented difunctionalization of the aryl ring at both the ipso and ortho positions relative to the original C–I bond