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Scalable Synthesis of Benzotriazoles via [3+2] Cycloaddition of Azides and Arynes in Flow
Author(s) -
Kleoff Merlin,
Boeser Lisa,
Baranyi Linda,
Heretsch Philipp
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001543
Subject(s) - aryne , cycloaddition , chemistry , azide , combinatorial chemistry , scalability , modular design , organic chemistry , catalysis , computer science , programming language , database
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.