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Rhodium(III)‐Catalyzed Annulative Carbooxygenation of 1,1‐Disubstituted Alkenes Triggered by C−H Activation
Author(s) -
Li Yang,
Tang Yuhai,
He Xin,
Shi Dandan,
Wu Jun,
Xu Silong
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201701703
Subject(s) - rhodium , chemistry , catalysis , amide , catalytic cycle , medicinal chemistry , redox , stereochemistry , organic chemistry
A Cp*Rh III ‐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 Rh III ‐Rh V ‐Rh III catalytic cycle.