A new reaction between alkyne and <i>N</i>-sulfonyl azide is presented. The reaction leads to novel synthons and proceeds to an intramolecular 1,3-dipolar cycloaddition reaction of the diazoalkene as a dipole component reacting with an arene as an unprecedented dipolarophile. The reaction pathway has been elucidated by characterizing the short-lived intermediates and is supported by DFT calculations. Tuning the substituents on the sulfonyl azide was found to pivot the reaction towards different pathways: intramolecular cycloaddition or Truce-Smiles type rearrangement. This reaction provides access to versatile organic frameworks; cyclic sulfonamide (sultam), fused sultam-pyrazole or substituted <i>NH</i>-triazole based on the preferred reaction pathway.

Arenes and diazoalkenes in 1,3-dipolar cycloaddition: An unexplored chemical space

ACS Spring 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.