Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols
(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 C 1-symmetric bis(arenol)s from the combination of C3- and C7-substituted 2-naphthols or phenols even when there is no...
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| Published in | Organic letters Vol. 22; no. 4; pp. 1469 - 1474 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
21.02.2020
Amer Chemical Soc |
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| Online Access | Get full text |
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| 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 C 1-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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| AbstractList | (Aqua)ruthenium(salen) complex
achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to selectively produce
-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. (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. (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 C 1-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. (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 C-1-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. (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.(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 | Uchida, Tatsuya Ueno, Takamasa Hayashi, Hiroki Kim, Chungsik |
| AuthorAffiliation | International Institute of Carbon-Neutral Energy Research (WPI-I2CNER) Faculty of Arts and Science Department of Chemistry, Graduate School of Science Kyushu University |
| AuthorAffiliation_xml | – name: Department of Chemistry, Graduate School of Science – name: Kyushu University – name: International Institute of Carbon-Neutral Energy Research (WPI-I2CNER) – name: Faculty of Arts and Science |
| Author_xml | – sequence: 1 givenname: Hiroki surname: Hayashi fullname: Hayashi, Hiroki organization: Faculty of Arts and Science – sequence: 2 givenname: Takamasa surname: Ueno fullname: Ueno, Takamasa organization: Kyushu University – sequence: 3 givenname: Chungsik surname: Kim fullname: Kim, Chungsik organization: Kyushu University – sequence: 4 givenname: Tatsuya orcidid: 0000-0002-6511-5752 surname: Uchida fullname: Uchida, Tatsuya email: uchida.tatsuya.045@m.kyushu-u.ac.jp organization: Kyushu University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31984748$$D View this record in MEDLINE/PubMed |
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| Keywords | BINOL DUAL ACTIVATION 2-NAPHTHOL DERIVATIVES PHENOLS KINETIC RESOLUTION BINAPHTHOL DERIVATIVES OXOVANADIUM(IV) COMPLEXES |
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| Snippet | (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to... (Aqua)ruthenium(salen) complex 1c achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to... (Aqua)ruthenium(salen) complex achieved good to high chemo- and enantioselective oxidative cross-coupling of arenols. The catalytic system can be used to... |
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| SubjectTerms | catalytic activity chemical bonding chemical structure Chemistry Chemistry, Organic chemoselectivity cross-coupling reactions enantioselectivity naphthols oxidation Physical Sciences ruthenium Science & Technology |
| Title | Ruthenium-Catalyzed Cross-Selective Asymmetric Oxidative Coupling of Arenols |
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