N-Heterocyclic Carbene Catalyzed Photoenolization/Diels–Alder Reaction of Acid Fluorides
The combination of light activation and N-heterocyclic carbene (NHC) organocatalysis has enabled the use of acid fluorides as substrates in a UVA-light-mediated photochemical transformation previously observed only with aromatic aldehydes and ketones. Stoichiometric studies and TD-DFT calculations support a mechanism involving the photoactivation of an ortho-toluoyl azolium intermediate, which exhibits “ketone-like” photochemical reactivity under UVA irradiation. Using this photo-NHC catalysis approach, a novel photoenolization/Diels–Alder (PEDA) process was developed that leads to diverse isochroman-1-one derivatives.
Agrawal, Arush,G?tze, Jan P.,Golz, Paul,Hopkinson, Matthew N.,Mavroskoufis, Andreas,Rajes, Keerthana,Ru?, Vincent
supporting information
p. 3190 - 3194
(2020/01/24)
Theoretical and experimental conformational preferences of the aldehyde and fluoroaldehyde groups in 2-methylbenzaldehyde, 2-trifluoromethylbenzaldehyde, and 4-chloro-2-methylbenzoyl fluoride. Proximate couplings
On the basis of long-range spin-spin coupling constants, the O-syn conformation of 2-methylbenzaldehyde in CCl4 solution at 305 K is favored over the O-anti form by a free energy of 0.5 kJ/mol.This number is compatible with other experiments, as well as w
Schaefer, Ted,Salman, Salman R.,Wildman, Timothy A.
p. 2364 - 2368
(2007/10/02)
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