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2 protocols using diphenylsilane

1

Synthesis of Allylated Catechol Derivatives

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m-Chloroperbenzoic acid (MCPBA), LiCl, tert-butylammonium fluoride (TBAF·3H2O), tert-butylammonium hydroxide (TBAH), 4-dimethylaminopyridine (DMAP), iBu3Al solution (25% in toluene), eugenol, 2,2-dimethoxy-2-phenylacetophenone (DMPA), t-butyldimethylsilyl chloride (TBDMSCl), thioglycolic acid, cysteamine and safrole were purchased from Sigma Aldrich. MePPh3Br and imidazole from Fluka, 1 M tert-butylammonium fluoride (TBAF) solution in THF from ChemCruz, and diphenylsilane and B(C6F5)3 from Alfa Aesar were used as received without any further purification. 4-Allylcatechol was prepared by reacting eugenol with LiCl in dimethyl formamide (DMF) as described.34 (link) Allyl glycidyl ether (AGE) from Sigma Aldrich was dried over CaH2 and distilled. Pb(AcO)4 was freshly prepared.35 Membrane (Spectra/Por) with a MWCO of 6000–8000 Daltons was purchased from Spectrum Laboratories, Inc.
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2

Synthesis of Bis(chloromethyl)dimethylsilane Derivatives

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All reactions were conducted under air atmosphere. All the solvents and chemicals were commercially available and were used as received. 1,4-diethynylbenzene (96%), Karstedt’s catalyst (platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex solution), anhydrous dichloromethane (≥99.8%), bis (chlorométhyl)dimethylsilane (97%), sodium azide (99%), N,N-dimethylformamide (99.8%), propargyl bromide (80 wt.% in toluene), copper bromide (98%), N,N-diisopropylethylamine (99%), 1,4-diethynylbenzene (96%), and absolute ethanol (≥99.8%) were purchased from Sigma-Aldrich (St. Quentin Fallavier, France). Diphenylsilane (97%), Bis (cyclopentadienyl) zirconium (IV) dihydride (ZrCp2H2), toluene, cyclohexane (+99%), magnesium sulfate (99.5%), ammonia (35% in water), diethylic ether (99%), and petroleum ether were obtained from Alfa-Aesar. Chloroform d1 (99.8%) and dimethylsulfoxide d6 (99.8%) were purchased from EurisoTop (Saint Aubin, France).
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