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

Daiki Doiuchi; Tatsuya Uchida

doi:10.1021/acs.orglett.1c02812

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

Daiki Doiuchi, Tatsuya Uchida

Division for Experimental Natural Science

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

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 language	English
Pages (from-to)	7301-7305
Number of pages	5
Journal	Organic letters
Volume	23
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.1c02812
Publication status	Published - Sept 17 2021

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.1c02812

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

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.",

author = "Daiki Doiuchi and Tatsuya Uchida",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant No. jp18H04264 in Precisely Designed Catalysis with Customized Scaffolding (to T.U.) and JP21J13680 (to D.D.). The International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan, is gratefully acknowledged. Publisher Copyright: {\textcopyright} 2021 American Chemical Society.",

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doi = "10.1021/acs.orglett.1c02812",

language = "English",

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journal = "Organic letters",

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T1 - Catalytic Highly Regioselective C-H Oxygenation Using Water as the Oxygen Source

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AU - Doiuchi, Daiki

AU - Uchida, Tatsuya

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant No. jp18H04264 in Precisely Designed Catalysis with Customized Scaffolding (to T.U.) and JP21J13680 (to D.D.). The International Institute for Carbon-Neutral Energy Research (WPI-I2CNER) from MEXT, Japan, is gratefully acknowledged. Publisher Copyright: © 2021 American Chemical Society.

PY - 2021/9/17

Y1 - 2021/9/17

N2 - 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.

AB - 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.

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

Abstract

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