BF3·SMe2 for Thiomethylation, Nitro Reduction and Tandem Reduction/SMe Insertion of Nitrogen Heterocycles
Herein, a general, solvent‐free and straightforward thiomethylation of electron deficient heterocycles using BF3· SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3· SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non‐malodorous reagent while the discovery of novel chemical transformations using BF3· SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent..
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2019 |
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| Erschienen: |
2019 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:2019 |
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| Enthalten in: |
European Journal of Organic Chemistry - 2019(2019), 31-32, Seite 5402-5408 |
| Beteiligte Personen: |
Söderström, Marcus [VerfasserIn] |
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| BKL: |
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| Anmerkungen: |
© 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Umfang: |
7 |
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| doi: |
10.1002/ejoc.201900503 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
WLY00505236X |
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| 520 | |a Herein, a general, solvent‐free and straightforward thiomethylation of electron deficient heterocycles using BF3· SMe2 as a dual thiomethyl source and Lewis acidic activator is presented. A range of heterocycles including pyrimidine, pyrazine, pyridazine, thiazole and purine derivatives were successfully substituted using this method. An unexpected reductive property of BF3· SMe2 towards nitropyridines was also discovered including an intriguing tandem reduction/SMe insertion process in certain substrates. Notable features of the present work include its convenience and use of a non‐malodorous reagent while the discovery of novel chemical transformations using BF3· SMe2 provides fundamental new insights into the reactivity of this commonly employed reagent. | ||
| 700 | 1 | |a Zamaratski, Edouard |4 aut | |
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