Abstract
Here we report a detailed theoretical study on the mechanism of NHCCu+ catalyzed domino rearrangement of (E)-N-(2-methyl-3-oxoprop-1-enyl)-N-haloamides. We find that the three substrates (fluoro-, chlorine- and bromine- substituted) can obtain stable imine products through the [1,3]-halogen rearrangement with the RDS barrier of less than 20 kcal/mol. Although the kinetic imine products are not thermodynamically very stable due to steric effect of di-substitution and destroyed aromatic benzyl, the isomerization of these kinetic products through further substitutes transfer is prohibited from very high reaction barriers.
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