A C3-symmetric amino–based organocatalyst can be easily prepared starting from chiral trans-N-Boc-1,2-diaminocyclohexane. Its activity on asymmetric synthesis of warfarin and analogues has been explored allowing moderate–high yields and good ster...
Artikel
Cooperative Covalent–Noncovalent Organocatalysis of the Knoevenagel Condensation Based on an Amine and Iodonium Salt Mixture
ChemCatChem, April 2024, DOI. Login für Volltextzugriff.
Von Wiley-VCH zur Verfügung gestellt
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.
Abstract
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.
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