Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

Hiroki Hayashi; Takamasa Ueno; Chungsik Kim; Tatsuya Uchida

doi:10.1021/acs.orglett.0c00048

Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

Hiroki Hayashi, Takamasa Ueno, Chungsik Kim, Tatsuya Uchida

Division for Experimental Natural Science

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

22 Citations (Scopus)

Abstract

(Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C₁-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.

Original language	English
Pages (from-to)	1469-1474
Number of pages	6
Journal	Organic letters
Volume	22
Issue number	4
DOIs	https://doi.org/10.1021/acs.orglett.0c00048
Publication status	Published - Feb 21 2020

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/acs.orglett.0c00048

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title = "Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols",

abstract = "(Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.",

author = "Hiroki Hayashi and Takamasa Ueno and Chungsik Kim and Tatsuya Uchida",

note = "Funding Information: Support by JSPS KAKENHI Grant JP18H04264 in Precisely Designed Catalysts with Customized Scaffolding and by the International Institute for Carbon-Neutral Energy Research (WPI-I 2 CNER) from MEXT, Japan, is gratefully acknowledged. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/acs.orglett.0c00048",

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T1 - Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

AU - Hayashi, Hiroki

AU - Ueno, Takamasa

AU - Kim, Chungsik

AU - Uchida, Tatsuya

N1 - Funding Information: Support by JSPS KAKENHI Grant JP18H04264 in Precisely Designed Catalysts with Customized Scaffolding and by the International Institute for Carbon-Neutral Energy Research (WPI-I 2 CNER) from MEXT, Japan, is gratefully acknowledged. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/2/21

Y1 - 2020/2/21

N2 - (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.

AB - (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce C1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no significant difference in oxidation potential between the cross-coupling partners. This unique cross-selectivity is dominated by steric rather than electronic effects of the arenols and can be controlled by chemoselective single-electron oxidation and oxidative carbon-carbon bond formation.

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Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols

Abstract

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