Record link: 
http://hdl.handle.net/20.500.12708/144877
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Title: 
Unsaturated Aryl and Heteroaryl N1-Tetrazoles from 1-Allyl-1H-tetrazole
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Citation: 
Seifried, M., Knoll, C., Welch, J., Müller, D., & Weinberger, P. (2018). Unsaturated Aryl and Heteroaryl N1-Tetrazoles from 1-Allyl-1H-tetrazole. Synthesis: Journal of Synthetic Organic Chemistry, 50(05), 1007–1014. https://doi.org/10.1055/s-0036-1591879
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Publisher DOI: 
10.1055/s-0036-1591879
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Publication Type: 
Article - Original Research Article
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Language: 
English
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Authors: 
Seifried, Marco 
Knoll, Christian 
Welch, Jan 
Müller, Danny 
Weinberger, Peter 
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Organisational Unit: 
E141-05 - Forschungsbereich Radiation Physics 
E166-02-2 - Forschungsgruppe Fluiddynamische Simulation (CFD) 
E163-01-3 - Forschungsgruppe Magneto- und Thermochemie 
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Journal: 
Synthesis: Journal of Synthetic Organic Chemistry 
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ISSN: 
0039-7881
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Date (published): 
11-Jan-2018
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Number of Pages: 
8
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Publisher: 
GEORG THIEME VERLAG KG
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Peer reviewed: 
Yes
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Keywords: 
spin crossover; Catalysis; cross coupling; Organic Chemistry; heterocycles; N1-substituted tetrazoles; Heck reaction; C-C bond formation; aqueous conditions
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Abstract: 
Unsaturated aryl- and heteroaryl N1-substituted tetrazoles have been exceedingly difficult to access but are nonetheless highly attractive for the preparation of novel multifunctional spin crossover materials. The development of a Heck cross-coupling protocol, featuring good substrate tolerance for aromatic and heteroaromatic substrates overcoming this synthetic challenge is presented. The combination of aqueous THF, triethylamine, and PdCl2/P(o-tolyl)3 gave fast reaction rates and good yields. Competition experiments with styrene evidenced a slight preference for reaction with 1-allyl-1H-tetrazole.
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Research Areas: 
Structure-Property Relationship: 100%
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Science Branch: 
Chemie
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