Organic Letters
Organic Letters
5 years ago

Ruthenium(II)-Catalyzed ortho-C–H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones

Ruthenium(II)-Catalyzed ortho-C–H Chalcogenation of Benzoic Acids via Weak O-Coordination: Synthesis of Chalcogenoxanthones
Harekrishna Sahoo, Gowri Sankar Grandhi, Suman Dana, Anup Mandal, Mahiuddin Baidya
A general protocol for direct chalcogenation of inert C–H bonds of (hetero)aromatic carboxylic acids is developed with a ruthenium(II) catalyst using readily available starting materials, offering densely substituted ortho-chalcogenyl aromatic acids in high yields (up to 96%). The strategy avoids the installation of an external directing group, use of metallic oxidants, and features operational simplicity with ample substrate scope. Synthetic application en route to biologically important chalcogenoxanthones is also demonstrated. This work represents the first example of ruthenium(II)-catalyzed direct C–H chalcogenation of benzoic acids.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b00996

DOI: 10.1021/acs.orglett.7b00996

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