Details
| Original language | English |
|---|---|
| Pages (from-to) | 979-982 |
| Number of pages | 4 |
| Journal | European Journal of Organic Chemistry |
| Volume | 2021 |
| Issue number | 6 |
| Early online date | 15 Dec 2020 |
| Publication status | Published - 8 Feb 2021 |
| Externally published | Yes |
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.
Keywords
- Arynes, Click chemistry, Cycloaddition, Flow chemistry, Nitrogen heterocycles
ASJC Scopus subject areas
- Chemistry(all)
- Physical and Theoretical Chemistry
- Chemistry(all)
- Organic Chemistry
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In: European Journal of Organic Chemistry, Vol. 2021, No. 6, 08.02.2021, p. 979-982.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Scalable Synthesis of Benzotriazoles via [3+2] Cycloaddition of Azides and Arynes in Flow
AU - Kleoff, Merlin
AU - Boeser, Lisa
AU - Baranyi, Linda
AU - Heretsch, Philipp
N1 - Funding Information: Financial support for this work was provided by the Boehringer Ingelheim Stiftung. We are grateful to Dr. Johannes Schwan, Dr. Reinhold Zimmer, and Nicole Fouquet (all Freie Universität Berlin) for preparative support. We acknowledge the assistance of the Core Facility BioSupraMol supported by the DFG. Open access funding enabled and organized by Projekt DEAL.
PY - 2021/2/8
Y1 - 2021/2/8
N2 - 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.
AB - 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.
KW - Arynes
KW - Click chemistry
KW - Cycloaddition
KW - Flow chemistry
KW - Nitrogen heterocycles
UR - http://www.scopus.com/inward/record.url?scp=85099183670&partnerID=8YFLogxK
U2 - 10.1002/ejoc.202001543
DO - 10.1002/ejoc.202001543
M3 - Article
VL - 2021
SP - 979
EP - 982
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
SN - 1434-193X
IS - 6
ER -