Cooperative Covalent–Noncovalent Organocatalysis of the Knoevenagel Condensation Based on an Amine and Iodonium Salt Mixture

The experimentally obtained kinetic data has indicated the existence of a synergetic cocatalytic effect provided by an iodonium salt in the base‐catalyzed Knoevenagel condensation. The diphenyliodonium triflate serving as the halogen bond‐donating Lewis acid provides the higher cocatalytic effect th...

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Published in:ChemCatChem 2024-06, Vol.16 (12), p.n/a
Main Authors: Sysoeva, Alexandra A., Il'in, Mikhail V., Bolotin, Dmitrii S.
Format: Article
Language:English
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Summary:The experimentally obtained kinetic data has indicated the existence of a synergetic cocatalytic effect provided by an iodonium salt in the base‐catalyzed Knoevenagel condensation. The diphenyliodonium triflate serving as the halogen bond‐donating Lewis acid provides the higher cocatalytic effect than zinc(II) triflate or triflic acid serving, respectively, as the metal cation‐based Lewis acid and Brønsted acid. Such a cocatalytic effect remains the same for a broad scope of carbonyl compounds covering aldehydes featuring electron‐withdrawing or electron‐donating substituents, as well as ketone involved in the reaction. A synergetic cocatalytic effect provided by an iodonium salt in the base‐catalyzed Knoevenagel condensation has been found. The diphenyliodonium triflate serving as the halogen bond‐donating Lewis acid provides the higher cocatalytic effect than zinc(II) triflate or triflic acid serving.
ISSN:1867-3880
1867-3899
DOI:10.1002/cctc.202301668