Journal of Organic Chemistry p. 9794 - 9797 (2015)
Update date:2022-08-16
Topics:
Gardner, Sean
Kawamoto, Takuji
Curran, Dennis P.
1,3-Dialkylimidazol-2-ylidene boranes have been made in moderate yields (typically 23-53%) from the corresponding N-alkyl imidazole, an alkylating agent (usually MeI), and sodium borohydride (NaBH4). The two-step, one-pot reaction sequence takes about 1 day to perform. The reagents are inexpensive, and the reactions are easy to conduct. The synthesis of 1,3-dimethylimidazol-2-ylidene borane has been conducted on scales up to 100 mmol and is especially convenient because the pure product can be isolated by direct recrystallization from water.
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