Positional Isomerization of 1,2-Azaborine through BN-Benzvalene
Abstract
A photochemical positional isomerization approach for converting readily accessible C5-aryl-1,2-azaborines into their C4-aryl counterparts via a BN-benzvalene intermediate is described. The oxidative radical cation pathway from BN-benzvalene to the C4-aryl products is supported by deuterium labeling experiments, transient absorption (TA) spectroscopy, and DFT calculations. The reaction's utility is demonstrated by providing the first general method to C4,C5-difunctionalized 1,2-azaborines and the regioselective synthesis of hexa-substituted derivatives.
Fields of Study & Subjects
Radical Photochemical Reactions
Organoboron and organosilicon chemistry
Catalytic C–H Functionalization Methods
Publication details
- Journal / source
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Volume
- 148
- Issue
- 3
- Pages
- 3820–3829
- Publication date
- 13 January 2026
- Language
- EN