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Ruthenium(II)-Catalyzed Regioselective C-8 Hydroxylation of 1,2,3,4-Tetrahydroquinolines.

A new interesting article has been published in Org Lett. 2018 Oct 23. doi: 10.1021/acs.orglett.8b02926. [Epub ahead of print] and titled:

Ruthenium(II)-Catalyzed Regioselective C-8 Hydroxylation of 1,2,3,4-Tetrahydroquinolines.

Authors of this article are:

Chen C, Pan Y, Zhao H, Xu X, Luo Z, Cao L, Xi S, Li H, Xu L.

A summary of the article is shown below:

Ru(II)-catalyzed chelation-assisted highly regioselective C8-hydroxylation of 1,2,3,4-tretrahydroquinolines has been developed. Various 1,2,3,4-tetrahydroquinolines underwent smooth C8-H hydroxylation with cheap and safe K2S2O8 as the oxidant and oxygen source to furnish the corresponding products in good to excellent yields with high tolerance of the functional groups. The choice of a readily installable and removable N-pyrimidyl directing group is the key to catalysis. Mechanistic studies suggest the involvement of a six-membered ruthenacycle intermediate in the catalytic cycle. The method can also be extended to the direct hydroxylation of other (hetero)arene C-H bonds.

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