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Copper-catalyzed synthesis of 5-substituted 1H-tetrazoles via the [3+2] cycloaddition of nitriles and trimethylsilyl azide

✍ Scribed by Tienan Jin; Fukuzou Kitahara; Shin Kamijo; Yoshinori Yamamoto

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
135 KB
Volume
49
Category
Article
ISSN
0040-4039

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✦ Synopsis

The [3+2] cycloaddition between various nitriles and trimethylsilyl azide proceeds smoothly in the presence of a Cu I catalyst in DMF/ MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of a copper azide species, followed by a successive [3+2] cycloaddition with the nitriles.

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ChemInform Abstract: Synthesis of 5-Subs
ChemInform Abstract: Synthesis of 5-Substituted 1H-Tetrazoles by the Copper-Catalyzed [3 + 2] Cycloaddition of Nitriles and Trimethylsilyl Azide.
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Regiospecific synthesis of 2-allylated-5
Regiospecific synthesis of 2-allylated-5-substituted tetrazoles via palladium-catalyzed reaction of nitriles, trimethylsilyl azide, and allyl acetates
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