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

被引：11

作者：

Doiuchi, Daiki ^{[1
]}

Uchida, Tatsuya ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Sci, Dept Chem, Fukuoka 8190395, Japan

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 18期

关键词：

BOND FUNCTIONALIZATION; MOLECULAR-STRUCTURE; COMPLEXES; HYDROXYLATION; ACTIVATION; OXIDATION; O-17; EPIMERIZATION; ALDOSES; ALKANE;

D O I：

10.1021/acs.orglett.1c02812

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：7301 / 7305

页数：5

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