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

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Catalytic Highly Regioselective C–H Oxygenation Using Water as the Oxygen Source: Preparation of 17O/18O-Isotope-Labeled Compounds
Organic Letters ( IF 4.9 ) Pub Date : 2021-09-08 , DOI: 10.1021/acs.orglett.1c02812
Daiki Doiuchi ₁ , Tatsuya Uchida _{1,

2}

Affiliation

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.

中文翻译：

以水为氧源的催化高区域选择性 C-H 氧化：17O/18O-同位素标记化合物的制备

我们发现水的氧原子通过 PhI(OOCR) _{2 的}可逆水解被活化为碘基苯衍生物，并可用作钌 (bpga) 催化的位点选择性 C-H 氧化的氧源。Ru(bpga)/PhI(OOCR) ₂ /H ₂ O 系统，空间上体积较小的各种化合物中的次甲基和亚甲基C-H 键可以以位点选择性方式转化为所需的氧官能团。使用这种方法，可以以多克规模制备氧同位素标记的化合物，例如d -[3- ¹⁷ O/ ¹⁸ O]-甘露糖。

更新日期：2021-09-17

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