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An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide–iron(ii) complexes

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Abstract

An enantioselective oxidative coupling of 2-naphthol derivatives is developed with the use of chiral Fe(II)–diphosphine oxide complexes. Optically active 1,1-bi-2-naphthol derivatives can be synthesized in high yields when a 2 : 1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is used in the presence of t-butyl hydroperoxide as an oxidant. The non-linear effect, X-ray crystal structure and ESI-MS suggest that a 2 : 1 complex of (S)-xylyl-iPrO-BIPHEP-oxide and Fe(OTf)2 is a pre-catalyst for a Fe(III)/Fe(IV) redox cycle.

Graphical abstract: An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide–iron(ii) complexes

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Publication details

The article was received on 06 Oct 2019, accepted on 17 Oct 2019 and first published on 17 Oct 2019


Article type: Communication
DOI: 10.1039/C9CC07834G
Chem. Commun., 2019, Advance Article

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    An enantioselective oxidative coupling reaction of 2-naphthol derivatives catalyzed by chiral diphosphine oxide–iron(II) complexes

    T. Horibe, K. Nakagawa, T. Hazeyama, K. Takeda and K. Ishihara, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC07834G

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