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- W2891702258 abstract "Rh-catalyzed cycloaddition–fragmentation of N-cyclopropylacrylamides is an effective method to directly obtain substituted azocanes. In this transformation, the challenging step is insertion of CO and alkene into the more hindered proximal cyclopropane CC bond while avoiding competitive less hindered proximal CC activation. Given the importance of this novel strategy, we performed a density functional theory study to clarify the catalytic mechanism. The calculations confirm that cleavage of the more hindered bond is more favorable than cleavage of the less hindered bond for Rh-catalyzed (7 + 1) cycloaddition of N-cyclopropylacrylamides. Comparison between Rh-catalyzed (3 + 1 + 2) and (7 + 1) cycloaddition shows that the coordination mode with different ligand plays a crucial role in enabling different CC cleavage. The main factors responsible for the occurrence of β-hydride elimination rather than CC reductive elimination are also discussed. The kinetic preference for β-hydride elimination can be attributed to the transition state of CC reductive elimination being more distorted and forming in a much more concerted fashion than that of β-hydride elimination. Additionally, C4H elimination is disfavored owing to weaker interaction energy compared with C7H elimination by analyzing using the distortion/interaction model." @default.
- W2891702258 created "2018-09-27" @default.
- W2891702258 creator A5060503404 @default.
- W2891702258 creator A5064711465 @default.
- W2891702258 creator A5088806426 @default.
- W2891702258 date "2018-11-01" @default.
- W2891702258 modified "2023-09-25" @default.
- W2891702258 title "Computational study of Rh(I)-Catalyzed Cycloaddition–Fragmentation of N-cyclopropylacrylamides" @default.
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- W2891702258 doi "https://doi.org/10.1016/j.tet.2018.09.034" @default.
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