Communication
ChemComm
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Based on the conventional Fe(III)/Fe(IV) redox mechanism
reported by Katsuki and Pappo,6a–d we propose the catalytic
cycle shown in Scheme 2. A pre-catalyst A is oxidized by 0.5 equiv.
of tBuOOH to give Fe(III) complex B. Subsequent oxidation of B by
another tBuOOH affords radical cation C, which tautomerizes to
high-valent Fe(IV) complex C0. A nucleophilic attack of 1a for
electrophilic C0 affords Fe(II) complex D. An Fe(III) tautomer D0
undergoes hydrogen-atom transfer by tBuOꢁ. The corresponding
(S)-2a is obtained upon a ligand exchange of E with 1a, which
regenerates B.
In summary, a chiral diphosphine oxide-Fe(II) complex has
been developed for the enantioselective oxidative coupling reaction
of 2-naphthols. A stable diphosphine oxide–Fe(II) complex acts as
an active oxidation catalyst in the presence of t-butyl hydroperoxide
as a readily available oxidant. This practical method facilitates
the construction of enantio-enriched 7,70- and 6,60-substituted
BINOLs. Moreover, the reaction likely proceeds via an Fe(III)/
Fe(IV) redox cycle, which is supported by mechanistic studies.
We believe that this study not only provides a method for the
synthesis of BINOLs, but also provides insight into the mechanism
of the oxidation properties of Fe(II) complexes for other relevant
Fe-catalyzed oxidation reactions.
4 For selected examples of vanadium-catalyzed enantioselective coupling,
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5 R. Irie, K. Masutani and T. Katsuki, Synlett, 2000, 1433.
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˜
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9 For selected reports of iron-catalyzed asymmetric oxidation, see;
´
(a) C. Duboc-Toia, S. Menage, C. Lambeaux and M. Fontecave,
Tetrahedron Lett., 1997, 38, 3727; (b) J. Legros and C. Bolm, Angew.
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Financial support was partially provided by JSPS KAKENHI
(Grant Numbers 15H05755, 15H05810, 17K14484 and 19K15560),
Fujifilm Corporation Award in Synthetic Organic Chemistry,
Japan and MEXT, Japan. Dr Hiroyasu Sato (Rigaku Corporation)
is acknowledged for assistance with X-ray analysis.
´
Chem. Soc., 2012, 134, 13538; ( f ) O. Cusso, M. Cianfanelli, X. Ribas,
R. J. M. K. Gebbink and M. Costas, J. Am. Chem. Soc., 2016, 138, 2732.
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(d) T. Horibe, S. Ohmura and K. Ishihara, J. Am. Chem. Soc., 2019, 141, 1877.
11 Recently, phosphine oxides have been shown to be suitable ligands
for Fe(II) in the oxidation reaction; T. Tanaka, K. Hashiguchi,
T. Tanaka, R. Yazaki and T. Ohshima, ACS Catal., 2018, 8, 8430.
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Conflicts of interest
There are no conflicts to declare.
Notes and references
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13680 | Chem. Commun., 2019, 55, 13677--13680
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