Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds

Daiki Doiuchi, Tatsuya Uchida

Research output: Contribution to journalArticlepeer-review

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-[3-17O/18O]-mannose can be prepared in a multigram scale.

Original languageEnglish
Pages (from-to)7301-7305
Number of pages5
JournalOrganic letters
Volume23
Issue number18
DOIs
Publication statusPublished - Sep 17 2021

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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