3 years ago

Rhodium(III)-Catalyzed Annulative Carbooxygenation of 1,1-Disubstituted Alkenes Triggered by C−H Activation

Rhodium(III)-Catalyzed Annulative Carbooxygenation of 1,1-Disubstituted Alkenes Triggered by C−H Activation
Yuhai Tang, Jun Wu, Silong Xu, Dandan Shi, Yang Li, Xin He
A Cp*RhIII-catalyzed annulative carbooxygenation of challenging 1,1-disubstituted alkenes triggered by C−H activation of N-aryloxyacetamides has been established, which affords 2,3-dihydrobenzofuran derivatives with a quaternary carbon center in good to excellent yields under mild redox-neutral conditions. An amide group on the alkenes is essential for the process, and may inhibit the β-H elimination from C(sp3)−Rh species by saturating the rhodium center through coordination. Furthermore, mechanistic insights obtained from control experiments suggest a mechanism involving a RhIII-RhV-RhIII catalytic cycle. Finding the right path: An efficient Cp*RhIII-catalyzed annulative carbooxygenation of challenging 1,1-disubstituted functionalized alkenes with N-aryloxyacetamides triggered by C−H activation is established. An amide group on alkenes is strategically introduced by inhibiting β-H elimination from C(sp3)−Rh species. Mechanistic investigations suggest that the mechanism most likely involves a RhIII-RhV-RhIII catalytic cycle.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201701703

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