Bypassing Ammonia: From N2 to Nitrogen Heterocycles without N1 Intermediates or Transition Metals

• Published in: Angewandte Chemie International Edition Vol. 63; no. 21; pp. e202402777 - n/a
• Main Authors: Weber, Marco, Kupfer, Thomas, Arrowsmith, Merle, Dewhurst, Rian D., Rang, Maximilian, Ritschel, Benedikt, Titlbach, Sven, Ernst, Martin, Rodrigues, Marieli O., Silva Júnior, Eufrânio N., Braunschweig, Holger
• Format: Journal Article
• Language: English
• Published: Weinheim Wiley Subscription Services, Inc 21.05.2024
• Edition: International ed. in English
• Subjects: Acetic anhydride; Ammonia; Boron; Heterocyclic compounds; Intermediates; main-group chemistry; metallomimetics; nitrogen heterocycles; nitrogen reduction reaction; Oxazole; Reagents; Sulfur; Transition metals
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.202402777

Diboradiazene compounds, derived in one step from the boron‐mediated reduction of dinitrogen (N2), were treated separately with sulfur and acetic anhydride, providing heterocyclic compounds that are BN isosteres of thiophene and 1,3‐oxazole, respectively. These simple reactions represent the final steps in two‐step routes to complex heterocycles from N2 that both circumvent the need for transition metal reagents and completely bypass the traditional intermediate ammonia. Two new heterocyclic species are prepared from diboradiazene compounds, thus completing two‐step routes to complex N‐heterocycles from N2 that both circumvent the need for transition metal reagents and completely bypass the traditional intermediate ammonia.