Development of a Rhodium(II)-Catalyzed Chemoselective C(sp(3) )-H Oxygenation
1MOE Key Laboratory of Protein Sciences, Department of Pharmacology and Pharmaceutical Sciences, School of Medicine and School of Life Sciences, Tsinghua University, Beijing, 100084 (P. R. China).
Abstract:
We report the first example of Rh(II) -catalyzed chemoselective double C(sp(3) )-H oxygenation, which can directly transform various toluene derivatives into highly valuable aromatic aldehydes with great chemoselectivity and practicality. The critical combination of catalyst Rh(OAc)2 , oxidant Selectfluor, and solvents of TFA/TFAA promises the successful delivery of the oxidation with satisfactory yields. A possible mechanism involving a unique carbene-Rh complex is proposed, and has been supported by both experiments and theoretical calculations.
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