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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Bibliographic Details
Published inOrganic letters Vol. 22; no. 4; pp. 1469 - 1474
Main Authors Hayashi, Hiroki, Ueno, Takamasa, Kim, Chungsik, Uchida, Tatsuya
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.02.2020
Amer Chemical Soc
Subjects
catalytic activity
chemical bonding
chemical structure
Chemistry
Chemistry, Organic
chemoselectivity
cross-coupling reactions
enantioselectivity
naphthols
oxidation
Physical Sciences
ruthenium
Science & Technology
BINOL
DUAL ACTIVATION
2-NAPHTHOL DERIVATIVES
PHENOLS
KINETIC RESOLUTION
BINAPHTHOL DERIVATIVES
OXOVANADIUM(IV) COMPLEXES
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Summary:(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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ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.0c00048