Journal of Organic Chemistry p. 3101 - 3110 (2015)
Update date:2022-09-26
Topics:
Ogiwara, Yohei
Takahashi, Keita
Kitazawa, Takefumi
Sakai, Norio
The combination of a catalytic amount of InCl3 and acetic anhydride remarkably promotes the Knoevenagel condensation of a variety of aldehydes and activated methylene compounds. This catalytic system accommodates aromatic aldehydes containing a variety of electron-donating and -withdrawing groups, heteroaromatic aldehydes, conjugate aldehydes, and aliphatic aldehydes. Central to successfully driving the condensation series is the formation of a geminal diacetate intermediate, which was generated in situ from an aldehyde and an acid anhydride with the assistance of an indium catalyst.
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