Continuous Flow Synthesis of Nitrosoarenes via Photochemical Rearrangement of Aryl Imines.

ABSTRACT: Nitrosoarenes are versatile organic building blocks; however, their intrinsic instability and limited synthetic accessibility have so far restricted their widespread use. Herein, we present a new continuous flow route toward these entities that is based on a direct photochemical rearrangement process using o-nitrophenylimines as starting materials. Due to the underlying redox mechanism, a new amide group accompanies the formation of the nitroso group. Crucial to the success of this approach is the use of trifluoroethanol as a solvent and high-power light-emitting diodes (365 nm) as light sources that provide uniform irradiation and high efficiency of the resulting continuous flow method. The process is fast and robust, with high functional group tolerance and high throughput. The fo

SUBMITTER: Garcia-Lacuna J 

PROVIDER: S-EPMC10777388 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature