- Use of Silylated Formiates as Hydrosilane Equivalents
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The present invention relates to a method for preparing organic compounds of formula (I) by reaction between a silylated formiate of formula (II) and an organic compound in the presence of a catalyst and optionally of an additive. The invention also relates to use of the method for preparing organic compounds of formula (I) for the preparation of reagents for fine chemistry and for heavy chemistry, as well as in the production of vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, and pesticides.
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- Photocatalyzed cross-dehydrogenative coupling of silanes with alcohols and water
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An efficient method for the dehydrogenative coupling of silanes with alcohols under photocatalysis was developed. The reaction proceeded in the presence of Ru(bpy)3Cl2(0.5 mol%) under visible light irradiation in acetonitrile at room temperature. The developed methodology was also applicable for the synthesis of silanols using water as a coupling partner.
- Lv, Haiping,Laishram, Ronibala Devi,Chen, Jingchao,Khan, Ruhima,Zhu, Yuanbin,Wu, Shiyuan,Zhang, Jianqiang,Liu, Xingyuan,Fan, Baomin
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supporting information
p. 3660 - 3663
(2021/04/16)
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- Mild synthesis of silyl ethers: Via potassium carbonate catalyzed reactions between alcohols and hydrosilanes
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A method has been developed for the silanolysis of alcohols using an abundant and non-corrosive base K2CO3 as a catalyst. Reactions between a variety of alcohols and hydrosilanes generate silyl ethers under mild conditions. The use of hydrosilanes leads to the formation of H2 as the only byproduct thus avoiding the formation of stoichiometric strong acids. The mild conditions lead to a wide scope of possible alcohol substrates and good functional group tolerance. Selective alcohol silanolysis is also observed in the presence of reactive C-H bonds, lending this method for extensive use in protection group chemistry.
- Delucia, Nicholas A.,Das, Nivedita,Vannucci, Aaron K.
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p. 3415 - 3418
(2018/05/23)
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- Iron-Catalyzed Silylation of Alcohols by Transfer Hydrosilylation with Silyl Formates
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An iron catalyst is shown for the first time to promote transfer hydrosilylation with silyl formates and is utilized for the silylation of alcohols. Attractive features of this protocol include the use of an earth-abundant transition-metal catalyst, mild reaction conditions, and the release of gases as the only byproducts (H 2 and CO 2).
- Godou, Timothé,Chauvier, Clément,Thuéry, Pierre,Cantat, Thibault
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p. 2473 - 2477
(2017/10/26)
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- Silylation of O-H bonds by catalytic dehydrogenative and decarboxylative coupling of alcohols with silyl formates
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The silylation of O-H bonds is a useful methodology in organic synthesis and materials science. While this transformation is commonly achieved by reacting alcohols with reactive chlorosilanes or hydrosilanes, we show herein for the first time that silylformates HCO2SiR3 are efficient silylating agents for alcohols, in the presence of a ruthenium molecular catalyst.
- Chauvier, Clément,Godou, Timothé,Cantat, Thibault
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supporting information
p. 11697 - 11700
(2017/11/03)
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- Dehydrogenative coupling of alcohol with hydrosilane catalyzed by an iron complex
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Silane alcoholysis of triethylsilane (Et3SiH) with alcohol (ROH) with the help of CpFe(CO)2Me (1) has been achieved to produce triethylsilyl ether (ROSiEt3) under the thermal condition. For some alcohols, the iron complex
- Fukumoto, Kozo,Kasa, Michiho,Nakazawa, Hiroshi
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p. 219 - 221
(2015/03/30)
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- Metal-free transfer hydrogenation of olefins via dehydrocoupling catalysis
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A major advance in main-group chemistry in recent years has been the emergence of the reactivity of main-group species that mimics that of transition metal complexes. In this report, the Lewis acidic phosphonium salt [(C 6F5)3PF][B(C6F5) 4] 1 is shown to catalyze the dehydrocoupling of silanes with amines, thiols, phenols, and carboxylic acids to form the Si-E bond (E = N, S, O) with the liberation of H2 (21 examples). This catalysis, when performed in the presence of a series of olefins, yields the concurrent formation of the products of dehydrocoupling and transfer hydrogenation of the olefin (30 examples). This reactivity provides a strategy for metal-free catalysis of olefin hydrogenations. The mechanisms for both catalytic reactions are proposed and supported by experiment and density functional theory calculations.
- Pérez, Manuel,Caputo, Christopher B.,Dobrovetsky, Roman,Stephan, Douglas W.
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p. 10917 - 10921
(2014/08/18)
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- Activation of silylphosphines by diethyl azodicarboxylate: Novel silylation of alcohols
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A novel activation mode of silylphosphines and an application of that to silylation of alcohols were described. Silylphosphines were found to be instantly activated by means of DEAD and PPTS to form reactive silyl cation equivalents. By using the activate
- Hayashi, Minoru,Matsuura, Yutaka,Watanabe, Yutaka
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p. 1409 - 1411
(2007/10/03)
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- Facile methods for the direct conversions of aryl acetates into the corresponding methoxymethyl ethers or silyl ethers
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Direct conversion of aryl acetates into aryl methoxymethyl ethers or aryl trialkylsilyl ethers was readily accomplished by treatment with methoxymethyl bromide or trialkylsilyl trifluoromethanesulfonate, respectively, in the presence of sodium methoxide.
- Oriyama, Takeshi,Noda, Kojiro,Sugawara, Satomi
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p. 2217 - 2223
(2007/10/03)
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