Unveiling New Reactivities in Complex Mixtures: Synthesis of Tricyclic Pyridinium Derivatives.

ABSTRACT: The discovery of new transformations drives the development of synthetic organic chemistry. While the main goal of synthetic chemists is to obtain the maximum yield of a desired product with minimal side product formation, meticulous characterization of the latter offers an opportunity for discovering new reaction pathways, alternative mechanisms, and new products. Herein, we present a case study on the discovery and development of a new chemical transformation using online mass spectrometry. This highly sensitive method enabled the discovery of a new reaction pathway in a catalyst-free cross-dehydrogenative coupling of 1,2,3,4-tetrahydroisoquinoline with acetone via peroxide intermediate, ultimately yielding a tricyclic pyridinium compound. Mass spectrometry was instrumental in detecting

SUBMITTER: Kootstra J 

PROVIDER: S-EPMC11826991 | biostudies-literature | 2025 Feb

REPOSITORIES: biostudies-literature