Efficient Generation of <i>ortho</i>‐Naphthoquinone Methides from 1,4‐Epoxy‐1,4‐dihydronaphthalenes and Their Annulation with Allyl Silanes

Sawama, Yoshinari; Shishido, Yuko; Yanase, Takayoshi; Kawamoto, Koichi; Goto, Ryota; Monguchi, Yasunari; Kita, Yasuyuki; Sajiki, Hironao

doi:10.1002/ange.201207315

Cited by 9 publications

(3 citation statements)

References 30 publications

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“…Compound 2: 1 H and 13 C NMR spectra of the product were identical to those reported in reference [3a]. 1 13 C NMR spectra of the product were identical to those reported in reference [26]. 1 159.…”

Section: Characterizationsupporting

confidence: 72%

“…On the other hand, silyl ethers are traditionally utilized for protection of the alcohol functionality and are tolerated under the nucleophilic conditions due to the low dissociative capacity of the siloxy functionality as a leaving group 11. Very recently, we discovered that silyl ethers are suitable substrates for iron‐catalyzed azidation reactions,12, 13 and other research groups have also reported the reactions between silyl ethers and reactive carbon nucleophiles, such as allylsilanes14 and enol acetates 15. Although Friedel–Crafts reactions with silyl ethers have been reported in the literature, only electron‐rich arenes could be adopted and a large excess of arene (as the solvent) was required 8.…”

Section: Introductionmentioning

confidence: 99%

“…: 1 H and13 C NMR spectra of the product were identical to those reported in reference [2j].1 H NMR (400 MHz, CDCl 3 ): d = 7.34 (d, J = 8.4 Hz, 1 H), 7.23-7.15 (m, 4 H), 7.11-7.07 (m, 1 H), 6.49 (dd, J = 8.4, 2.4 Hz, 1 H), 6.38 (d, J = 2.4 Hz, 1 H), 3.80 (s, 3 H), 3.33 (s, 3 H), 1.64 ppm (s, 6 H); 13 C NMR (100 MHz, CDCl 3 ): d = 159.4, 151.7, 131.2, 127.5, 127.0, 125.6, 125.5, 124.7, 103.5, 100.6, 55.2, 55.1, 41.4, 29.8, 29.7 ppm.…”

mentioning

confidence: 99%

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Iron‐Catalyzed Friedel–Crafts Benzylation with Benzyl TMS Ethers at Room Temperature

Sawama

Shishido

Kawajiri

et al. 2013

Chemistry A European J

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Friedel-Crafts benzylations between unactivated arenes and benzyl alcohol derivatives are clean and straightforward processes to construct biologically useful di- and tri-arylmethanes. We have established an efficient iron-catalyzed Friedel-Crafts benzylation method at room temperature that uses benzyl TMS ethers as substrates, which are poorly reactive under common nucleophilic substitution conditions. The reaction seems to progress through iron-catalyzed self-condensation of the benzyl TMS ether to the corresponding dibenzylic ether. The use of excess arene relative to benzyl TMS ether produced mono-benzylated arene (di- and tri-arylmethane products), whereas the use of excess benzyl TMS ether versus arene provided bis-benzylated arene (polyarylated products) in high yields and regioselectivities. In previous methods, the latter double Friedel-Crafts benzylations hardly proceed.

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Section: Characterizationsupporting

confidence: 72%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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Iron‐Catalyzed Friedel–Crafts Benzylation with Benzyl TMS Ethers at Room Temperature

Sawama

Shishido

Kawajiri

et al. 2013

Chemistry A European J

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CH Functionalization/CO Bond Cleavage of Benzyl Silyl Ethers with Ynamides for the Chemoselective Synthesis of Skeletally Diverse Compounds

et al. 2016

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Described here is ap ractical carbocationinitiated formal [3 + + 2] or [4 + + 2] cycloaddition reaction for the diversity-oriented syntheses of 1-amidoindenes and 2-amido-4H-chromenes.T he Lewis acid-promoted annulation of ynamides andb enzyl silyl ethers efficiently constructs1 -amidoindenes via C À Hf unctionalization of benzyls ilyl ethers.B yu tilization of o-methoxybenzyl silyl ethers,2 -amido-4H-chromenes are also constructed via C À Ob ond cleavage of benzyl silyl ethers.

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Site‐Selective Iron(III) Chloride‐Catalyzed Arylation of 4‐Aryl‐4‐methoxy‐2,5‐cyclohexadienones for the Synthesis of Polyarylated Phenols

et al. 2016

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Thei ron(III) chloride-catalyzedF riedel-Crafts arylation of 4-aryl-4-methoxy-2,5-cyclohexadienones,w hich were easily preparedb yt he phenyliodine(III) diacetate (PIDA)-mediated oxidation of 4-arylphenols in methanol, proceededs ite-selectively to form meta-terphenyl( 2,4-diarylphenol) derivatives in good yields.T he subsequent PIDAmediated oxidation and iron(III) chloride-catalyzed Friedel-Crafts arylation of the resulting products gave the corresponding 2,4,6-triarylphenol derivatives.T he present method providesu seful highly substituted polyarylated compounds.

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Efficient Generation of ortho‐Naphthoquinone Methides from 1,4‐Epoxy‐1,4‐dihydronaphthalenes and Their Annulation with Allyl Silanes

Cited by 9 publications

References 30 publications

Iron‐Catalyzed Friedel–Crafts Benzylation with Benzyl TMS Ethers at Room Temperature

Iron‐Catalyzed Friedel–Crafts Benzylation with Benzyl TMS Ethers at Room Temperature

CH Functionalization/CO Bond Cleavage of Benzyl Silyl Ethers with Ynamides for the Chemoselective Synthesis of Skeletally Diverse Compounds

Site‐Selective Iron(III) Chloride‐Catalyzed Arylation of 4‐Aryl‐4‐methoxy‐2,5‐cyclohexadienones for the Synthesis of Polyarylated Phenols

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