Oxidative coupling polymerization of octahydroxyquaternaphthyl derivatives producing stereocontrolled polybinaphthol

Habaue, Shigeki; Ishikawa, Kazutaka; Aikawa, Akiko; Murakami, Soichiro; Hatano, Bunpei

doi:10.1007/s00289-006-0565-8

Cited by 7 publications

(5 citation statements)

References 19 publications

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“…728 However, using the PhBox ligand completely overrides the stereochemistry of the monomer, resulting in complete ligand control (Scheme 412), an effect seen both with both binaphthol and trinaphthol monomers, 686,729 as well as dihydroxyquaternaphthyl derivatives (Scheme 413). 730 …”

Section: Reactions Of Phenols and Naphtholsmentioning

confidence: 99%

“…While a matched case can give up to 84:16 ( R )/( S ) ratio of axial stereocenters in the product, a mismatched case can drop the ratio to nearly 1:1 (Scheme ) . However, using the PhBox ligand completely overrides the stereochemistry of the monomer, resulting in complete ligand control (Scheme ), an effect seen both with both binaphthol and trinaphthol monomers, , as well as dihydroxyquaternaphthyl derivatives (Scheme ) …”

Section: Reactions Of Phenols and Naphtholsmentioning

confidence: 99%

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Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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Section: Reactions Of Phenols and Naphtholsmentioning

confidence: 99%

Section: Reactions Of Phenols and Naphtholsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…The tetrahydroxybinaphthyl derivative, THBN, is an interesting monomer for the OCP leading to an optically-active polymer with a rigid main chain constructed from continuous binaphthol units [28,29]. This monomer has a phenol framework with a methoxy group at the o-position, therefore, could be copolymerized with DMP.…”

Section: Resultsmentioning

confidence: 99%

“…2 , TCI], and N,N'-diethylethylenediamine (DEEDA, Wako), were used as received. The tetrahydroxybinaphthyl derivative, 3,3'-dihydroxy-2,2'-dimethoxy-1,1'-binaphthalene (THBN), was synthesized as previously reported [28,29].…”

Section: Introductionmentioning

confidence: 99%

Effective Synthesis of Poly(2,6-Dimethyl-1,4-Phenylene Oxide) Derivatives by Oxidative Coupling Copolymerization of Alkoxyphenols with Copper(II) Catalyst

Takamushi

Ito

Sakaki

et al. 2017

J. Adv. Catal. Sci. Techno.

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The oxidative coupling copolymerization between 2,6-dimethylphenol (DMP) and phenols having various alkoxy groups, such as methyoxy (MOP), ethoxy, benzyloxy, butoxy, and 2-hydroxyethoxy groups, was carried out using a copper(II) catalyst under an O2 atmosphere. The copolymerizations with alkoxyphenols effectively proceeded, and the unit ratios of the obtained copolymers were in good agreement with those in the feed. The coupling regioselectivity, such as oxyphenylene (CO) and phenylene (CC), of the alkoxyphenol unit constructed during the copolymerization was also estimated by the 1 H NMR analysis of the acetylated polymer. As an example, the copolymer with the unit ratios of DMP:p-MOP = 50:50 and CO:CC = 67:33, was obtained in 71% yield during the copolymerization with p-MOP (feed ratio, 50:50) in a mixed solvent of CH2Cl2 and methanol (7/1 (v/v)) for 24 h. The solubility and thermal property of the obtained copolymers were significantly affected by the structure of alkoxyphenol unit. disubstituted phenols, such as 2-allyl-6-methylphenol and 2,6-diphenylphenol, as a comonomer [11][12][13][14]. Scheme 1: Active species for oxidative coupling polymerization of DMP.Scheme 2: Monomers used for copolymerization. Scheme 3: Oxidative coupling copolymerization between DMP and alkoxyphenols.

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“…An analogous and more detailed result was obtained by studying the AOCP reactions of rac -( S )- and rac -( R )-2,2′-methoxy-1,1′-binaphthalene-3,3′-diols ( 461 , R = Me). They were catalyzed by [( S )- 1 /CuCl] or [( R )- 1 /CuCl] complexes (Scheme ), and both the estimated stereochemistry of the newly formed C–C bond ( S : R ) in the polymers 462 and the [α] D values reported in Table (entries 4–8) suggest that the reactions of ( R )- and ( S )- 461 with [( S )- 1 /CuCl] afford polymers with preferential (... SSSS ...) and (... RSRS ...) chain structures, respectively (Table , entries 5 and 6). , …”

Section: Two Commercial Ligands As Box Prototypes: Reactions Using 4-...mentioning

confidence: 99%

Update 1 of: C₂-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis

2011

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In 1991 two back-to-back communications appeared in The Journal of the American Chemical Society: one by Evans et al. dealt with the asymmetric cyclopropanation of alkenes 9 and a second one by Corey et al. that covered enantioselective DielsÀAlder reactions. 10 They reported the use of chiral Cu(I)À and Fe(III)Àbox complexes as catalysts, respectively.These two communications induced a small revolution in the field of asymmetric catalysis. The box ligands quickly became widely adopted as bidentate ligands for their easy and flexible synthesis and for the excellent enantioselectivity induced first in two very useful reactions, and later in a large variety of other reactions. These communications also anticipated the usual research protocol to be ultimately used in box chemistry: (a) synthesis of the ligand following a sequence that, for a long time, would become a standard (reaction of dialkylmalonyl dichloride with an optically active 1,2-amino alcohol, conversion of the bis-hydroxyamide to the corresponding bis-chloroamide, and ring closure under basic conditions); (b) preparation of the chiral catalyst by reaction of the box ligand with an inorganic salt [CuOTf and FeCl 2 /I 2 ]; (c) test of the chiral Lewis acid complex as a catalyst for asymmetric induction in the reaction; (d) proposal of a reacting intermediate in which the PR286 dx.

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Oxidative coupling polymerization of octahydroxyquaternaphthyl derivatives producing stereocontrolled polybinaphthol

Cited by 7 publications

References 19 publications

Aerobic Copper-Catalyzed Organic Reactions

Aerobic Copper-Catalyzed Organic Reactions

Effective Synthesis of Poly(2,6-Dimethyl-1,4-Phenylene Oxide) Derivatives by Oxidative Coupling Copolymerization of Alkoxyphenols with Copper(II) Catalyst

Update 1 of: C₂-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis

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Oxidative coupling polymerization of octahydroxyquaternaphthyl derivatives producing stereocontrolled polybinaphthol

Cited by 7 publications

References 19 publications

Aerobic Copper-Catalyzed Organic Reactions

Aerobic Copper-Catalyzed Organic Reactions

Effective Synthesis of Poly(2,6-Dimethyl-1,4-Phenylene Oxide) Derivatives by Oxidative Coupling Copolymerization of Alkoxyphenols with Copper(II) Catalyst

Update 1 of: C2-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis

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Update 1 of: C₂-Symmetric Chiral Bis(oxazoline) Ligands in Asymmetric Catalysis