Title:
Scalable Synthesis of Benzotriazoles via [3+2] Cycloaddition of Azides and Arynes in Flow
Author(s):
Kleoff, Merlin; Boeser, Lisa; Baranyi, Linda; Heretsch, Philipp
Year of publication:
2021
Available Date:
2021-02-09T07:18:42Z
Abstract:
A method for the metal-free synthesis of benzotriazoles in flow is reported. Using azides and in situ generated arynes, benzotriazoles are formed in a [3+2] cycloaddition within minutes. Employing different substitution patterns of the azide and aryne coupling partners, a modular access to benzotriazoles is provided. Thermal strain of hazardous azides and accumulation of reactive intermediates is minimized by short reaction times in flow, improving the safety profile of the process. The scalability of the reaction is demonstrated.
Part of Identifier:
e-ISSN (online): 1099-0690
Keywords:
Arynes
Click chemistry
Cycloaddition
Flow chemistry
Nitrogen heterocycles
DDC-Classification:
540 Chemie und zugeordnete Wissenschaften
Publication Type:
Wissenschaftlicher Artikel
URL of the Original Publication:
DOI of the Original Publication:
Journaltitle:
European Journal of Organic Chemistry
Department/institution:
Biologie, Chemie, Pharmazie
Institut für Chemie und Biochemie