Computational Exploration of RhIII/RhV and RhIII/RhI Catalysis in Rhodium(III)-Catalyzed C–H Activation Reactions of N-Phenoxyacetamides with Alkynes

Yun-Fang Yang, K. N. Houk and Yun-Dong Wu

J. Am. Chem. Soc.,
2016, 138 (21), pp 6861–6868; DOI: 10.1021/jacs.6b03424


The Houk group and Wu group report density functional theory (B3LYP and M06) investigations on the mechanism of rhodium(III)-catalyzed redox coupling reaction of N-phenoxyacetamides with alkynes. The results elucidated the role of the internal oxidizing directing group, and the role of RhIII/RhI and RhIII/RhV catalysis of C–H functionalizations. A novel RhIII–RhV–RhIII cycle successfully rationalizes the recent experimental observations.

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