AI Article Synopsis
- A new method using Ru(II) catalyst allows for highly selective C8-hydroxylation of 1,2,3,4-tetrahydroquinolines, resulting in good to excellent yields.
- The process uses inexpensive and safe KSO for oxidation, demonstrating excellent compatibility with various functional groups.
- Key to this method is a removable N-pyrimidyl directing group, and studies indicate the formation of a six-membered ruthenacycle intermediate during the reaction.
Article Abstract
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 KSO 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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| http://dx.doi.org/10.1021/acs.orglett.8b02926 | DOI Listing |
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