Journal
CHEMICAL SCIENCE
Volume 8, Issue 8, Pages 5713-5720Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc00964j
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Funding
- University of Geneva
- Swiss National Science Foundation
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Using N-sulfonyl triazoles as substrates, compounds as diverse as 2-imino tetrahydrofurans, 13- and 15-membered ring aza-macrocycles can be prepared selectively via formal [1 + 4], [5 + 4 + 4] and [3 + 4 + 4 + 4] condensations of alpha-imino carbenes and oxetanes under Rh(II)-catalysis or thermal activation. Spirocyclic N-heterocycles are also accessible by means of Buchwald-Hartwig and Pictet-Spengler cyclizations. By reaction control, substrate selection or further derivatization, a large variety of chemical structures is thus achievable. Finally, using triazoles reacting under thermal activation, interesting mechanistic insight was obtained.
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