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

共 55 条

[51] Understanding the Oxidative Relationships of the Metal Oxo, Hydroxo, and Hydroperoxide Intermediates with Manganese(IV) Complexes Having Bridged Cyclams: Correlation of the Physicochemical Properties with Reactivity [J].

Yin, Guochuan .

ACCOUNTS OF CHEMICAL RESEARCH, 2013, 46 (02) :483-492

[52] Prediction of aqueous pKa values of hydroxybenzoic acid using hydrogen-bonded complexes with ammonia [J].

Zhang, Jian-Dong ;

Zhu, Qing-Zhen ;

Li, Shu-Jin ;

Tao, Fu-Ming .

CHEMICAL PHYSICS LETTERS, 2009, 475 (1-3) :15-18

[53] Labeling Monosaccharides With Stable Isotopes [J].

Zhang, Wenhui ;

Zhao, Shikai ;

Serianni, Anthony S. .

ISOTOPE LABELING OF BIOMOLECULES - LABELING METHODS, 2015, 565 :423-458

[54] para-Selective C-H bond functionalization of iodobenzenes [J].

Zhao, Ying ;

Yan, Haiming ;

Lu, Hanwei ;

Huang, Zhiliang ;

Lei, Aiwen .

CHEMICAL COMMUNICATIONS, 2016, 52 (76) :11366-11369

[55] A PRACTICAL, EFFICIENT LARGE-SCALE SYNTHESIS OF 1,6-ANHYDROHEXOPYRANOSES [J].

ZOTTOLA, MA ;

ALONSO, R ;

VITE, GD ;

FRASERREID, B .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (26) :6123-6125

← 1 2 3 4 5 6 →