期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 17, 页码 11150-11160出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01868
关键词
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资金
- National Natural Science Foundation of China [21873055, 21702119]
- Natural Science Foundation of Shandong Province, China [ZR2019MB016]
The Rh(III)-catalyzed oxidative coupling of oxime ether (S1) and cyclopropanol (S2) with Cu(II) as the oxidant features the combination of C-H activation and strained ring opening. The sequential order of C-H activation versus ring en opening was investigated with the aid of density functional theory calculations. Prior ring opening due to the release of ring strain is found to be favored over the prior C-H activation. For the prior ring-opening mechanisms, the outer-sphere concerted metalation-deprotonation (CMD) mechanism in C-H bond activation is energetically favored. The outer-sphere CMD mechanism proposed in this work favors solvent effects and affords the N -> Rh binding that allows a directing role of the Schiff base group. In conclusion, the reaction was suggested to undergo prior ring opening followed by C-H activation via the outer-sphere CMD mechanism.
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