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Chemistry. 2015 Oct 12;21(42):14937-42. doi: 10.1002/chem.201502140. Epub 2015 Aug 27.

Development of a Rhodium(II)-Catalyzed Chemoselective C(sp(3) )-H Oxygenation.

Author information

1
MOE 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).
2
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 (P. R. China).
3
School of Chemistry and Chemical Engineering, Chongqing University, Chongqing, 400030 (P. R. China). lanyu@cqu.edu.cn.
4
MOE 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). yrao@mail.tsinghua.edu.cn.

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.

KEYWORDS:

C(sp3)H oxygenation; carbene-Rh complex; chemoselective; oxidant; rhodium(II) catalyst

PMID:
26311544
DOI:
10.1002/chem.201502140

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