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• W2413250654 endingPage "8121" @default.
• W2413250654 startingPage "8113" @default.
• W2413250654 abstract "Density functional theory calculations were conducted to develop a mechanistic understanding of the Rh(III)-catalyzed C-H activation/cycloaddition reactions of N-phenoxyacetamide and N-pivaloxybenzamide with cyclopropenes, and insights into the substrate-dependent chemoselectivity were provided. The results showed that the divergence originated from the different reactivity of the seven-membered rhodacycles from the insertion of cyclopropene into the Rh-C bond. In reactions of N-pivaloxybenzamide, such an intermediate undergoes the pivalate migration to form a cyclic Rh(V)-nitrenoid intermediate in a reaction that is easier than the opening of the three-membered ring by β-carbon elimination, leading finally to a tricyclic product with retention of the cyclopropane moiety by facile reductive elimination. While similar Rh(V)-nitrenoid species could also be possibly formed in Cp*Rh(III)-catalyzed reactions of N-phenoxyacetamide, the β-carbon elimination occurs more easily from the corresponding seven-membered rhodacycle intermediate and the subsequent O-N bond cleavage gives rise to an unexpected dearomatized (E)-6-alkenylcyclohexa-2,4-dienone intermediate. The E/Z isomerization of this intermediate is required for the final cyclization to 2H-chromene, and interesting metal-ligand cooperative catalysis with Rh(III) carboxylate was disclosed in the C═C double bond rotation process." @default.
• W2413250654 created "2016-06-24" @default.
• W2413250654 creator A5011920818 @default.
• W2413250654 creator A5029978416 @default.
• W2413250654 date "2015-08-10" @default.
• W2413250654 modified "2023-10-07" @default.
• W2413250654 title "Mechanistic Understanding of the Divergent Reactivity of Cyclopropenes in Rh(III)-Catalyzed C–H Activation/Cycloaddition Reactions of <i>N</i>-Phenoxyacetamide and <i>N</i>-Pivaloxybenzamide" @default.
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