Journal of Organometallic Chemistry p. 83 - 87 (2017)
Update date:2022-08-11
Topics:
Yamada, Mizuki
Matsumura, Mio
Kawahata, Masatoshi
Murata, Yuki
Kakusawa, Naoki
Yamaguchi, Kentaro
Yasuike, Shuji
Trisubstituted 5-stibano-1H-1,2,3-triazoles 3 was synthesized by the Cu-catalyzed [3 + 2] cycloaddition of ethynylstibane 1 with benzyl azide 2 in the presence of CuBr (5 mol%) under aerobic conditions. 5-Stibanotriazole 3 was treated with an equimolecular amount of phenyllithium (PhLi) in anhydrous THF under argon atmosphere at ?78 °C. Subsequent treatment with various electrophiles formed 1,4,5-trisubstituted-1,2,3-triazoles 5 containing a benzyl moiety. This reaction is a novel example of an antimony (Sb) – lithium (Li) exchange reaction for the functionalization of heterocycles.
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