Catalytic Highly Regioselective C–H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
- 8 September 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 23 (18), 7301-7305
- https://doi.org/10.1021/acs.orglett.1c02812
Abstract
We found that the oxygen atom of water is activated to iodosylbenzene derivatives via reversible hydrolysis of PhI-(OOCR)(2) and can be used to the oxygen source for ruthenium(bpga)-catalyzed site-selective C-H oxygenation. Ru(bpga)/PhI-(OOCR)(2)/H2O system, sterically less bulky methinic and methylenic C-H bonds in various compounds can be converted to desired oxygen functional groups in a site-selective manner. Using this method, oxygen-isotope labeled compounds such as D-[3-O-17/O-18]-mannose can be prepared in a multigram scale.Keywords
Funding Information
- Japan Society for the Promotion of Science (JP18H04264, JP21J13680)
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