Senior Investigators: Prof. John Hartwig (UC-Berkeley), Prof. William Jones (U. Rochester)

Aniline is produced on a billion pound per year scale as a starting material for many chemicals including dyes, polyurethane and other plastics, herbicides and specialty fibers. The current synthesis of aniline relies on old, well- known chemistry that has been optimized. To further improve upon the synthesis, new chemistry must be developed. The simplest and most direct synthesis of aniline from benzene would use ammonia as the source of nitrogen, however this reaction is not thermodynamically favored. The strategy CENTC is investigating involves the oxidative addition of N-O bonds, such as the intramolecular amination of 1,1-diarylpropan-2-one O-acetyl oximes to form indole products shown below. Our current focus is designing new strategies to accomplish intermolecular amination of unactivated arenes with hydroxylamine derivatives.