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J Am Chem Soc. 2015 Feb 18;137(6):2191-4. doi: 10.1021/ja5126885. Epub 2015 Feb 4.

Metalation of a thiocatechol-functionalized Zr(IV)-based metal-organic framework for selective C-H functionalization.

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Department of Chemistry and Biochemistry, University of California, San Diego , La Jolla, California 92093, United States.


The incorporation of 2,3-dimercaptoterephthalate (thiocatecholate, tcat) into a highly robust UiO-type metal-organic framework (MOF) has been achieved via postsynthetic exchange (PSE). The anionic, electron-donating thiocatecholato motif provides an excellent platform to obtain site-isolated and coordinatively unsaturated soft metal sites in a robust MOF architecture. Metalation of the thiocatechol group with palladium affords unprecedented Pd-mono(thiocatecholato) moieties within these MOFs. Importantly, Pd-metalated MOFs are efficient, heterogeneous, and recyclable catalysts for regioselective functionalization of sp(2) C-H bond. This material is a rare example of chelation-assisted C-H functionalization performed by a MOF catalyst.


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