Role of base assisted proton transfer in N-heterocyclic carbene-catalyzed intermolecular Stetter reaction
The mechanism of the NHC-catalyzed intermolecular Stetter reaction between
benzaldehyde and cyclopropene has been investigated using the PCM-M062X/6-311++ G
(3df, 2p)//M062X/6-31+ G (d, p) level of DFT. Compared to the direct reaction, a substantial
reduction in the activation free energy by 10.6–14.4 kcal/mol is observed when the reaction
is performed in the presence of water, 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene (TBD), and 1, 8-
diazabicyclo [5.4. 0] undec-7-ene (DBU). The bases promote the proton transfer step of the …
benzaldehyde and cyclopropene has been investigated using the PCM-M062X/6-311++ G
(3df, 2p)//M062X/6-31+ G (d, p) level of DFT. Compared to the direct reaction, a substantial
reduction in the activation free energy by 10.6–14.4 kcal/mol is observed when the reaction
is performed in the presence of water, 1, 5, 7-triazabicyclo [4.4. 0] dec-5-ene (TBD), and 1, 8-
diazabicyclo [5.4. 0] undec-7-ene (DBU). The bases promote the proton transfer step of the …